# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd211287 #TrackingRef 'cd211287.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H60 O6' _chemical_formula_weight 600.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4149(8) _cell_length_b 13.7246(11) _cell_length_c 24.6030(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3516.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4094 _cell_measurement_theta_min 4.447 _cell_measurement_theta_max 47.659 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.233 _exptl_crystal_size_mid 0.179 _exptl_crystal_size_min 0.163 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.62106 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19081 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6874 _reflns_number_gt 4976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0868P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.6(12) _chemical_absolute_configuration ad _refine_ls_number_reflns 6874 _refine_ls_number_parameters 426 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.009 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35779(19) -0.08810(12) 0.83069(7) 0.0579(5) Uani 1 1 d . A . O3 O 0.71015(15) 0.18701(13) 0.84632(7) 0.0500(4) Uani 1 1 d . B . O2 O 0.2524(11) -0.0829(8) 0.7511(4) 0.099(3) Uani 0.60 1 d P A 1 O4 O 0.8595(8) 0.2094(5) 0.9100(4) 0.088(2) Uani 0.60 1 d P B 1 O2' O 0.2029(14) -0.0800(13) 0.7705(5) 0.094(4) Uani 0.40 1 d P A 2 O4' O 0.8481(13) 0.1504(9) 0.9126(6) 0.113(4) Uani 0.40 1 d P B 2 O5 O 0.12164(15) 0.49265(11) 0.95593(7) 0.0494(4) Uani 1 1 d U . . O6 O 0.17161(17) 0.67557(13) 0.99171(8) 0.0598(5) Uani 1 1 d . . . H6 H 0.1508 0.6194 0.9844 0.090 Uiso 1 1 calc R . . C1 C 0.2459(2) 0.15242(17) 0.88607(11) 0.0486(6) Uani 1 1 d . . . H1A H 0.1783 0.1670 0.9120 0.058 Uiso 1 1 calc R . . H1B H 0.2247 0.1848 0.8522 0.058 Uiso 1 1 calc R . . C2 C 0.2497(3) 0.04225(19) 0.87637(12) 0.0563(7) Uani 1 1 d . . . H2A H 0.2644 0.0088 0.9105 0.068 Uiso 1 1 calc R . . H2B H 0.1680 0.0206 0.8619 0.068 Uiso 1 1 calc R . . C3 C 0.3551(3) 0.01792(17) 0.83711(11) 0.0511(6) Uani 1 1 d . . . H3 H 0.3336 0.0469 0.8019 0.061 Uiso 1 1 calc R . . C4 C 0.4911(2) 0.05061(18) 0.85271(10) 0.0478(6) Uani 1 1 d . . . C5 C 0.4824(2) 0.16274(17) 0.86641(9) 0.0403(5) Uani 1 1 d . . . H5 H 0.4592 0.1942 0.8320 0.048 Uiso 1 1 calc R . . C6 C 0.6079(2) 0.21220(17) 0.88405(10) 0.0418(6) Uani 1 1 d . . . H6A H 0.6310 0.1910 0.9208 0.050 Uiso 1 1 calc R . . C7 C 0.5967(2) 0.32296(18) 0.88241(10) 0.0443(6) Uani 1 1 d . . . H7A H 0.5800 0.3431 0.8453 0.053 Uiso 1 1 calc R . . H7B H 0.6782 0.3510 0.8933 0.053 Uiso 1 1 calc R . . C8 C 0.4912(2) 0.36369(16) 0.91905(9) 0.0386(5) Uani 1 1 d . . . C9 C 0.3646(2) 0.30749(16) 0.90565(9) 0.0387(5) Uani 1 1 d . . . H9 H 0.3475 0.3226 0.8674 0.046 Uiso 1 1 calc R . . C10 C 0.3733(2) 0.19354(16) 0.90762(10) 0.0403(5) Uani 1 1 d . . . C11 C 0.2492(2) 0.35055(16) 0.93662(10) 0.0437(6) Uani 1 1 d . . . H11A H 0.1719 0.3160 0.9260 0.052 Uiso 1 1 calc R . . H11B H 0.2616 0.3407 0.9753 0.052 Uiso 1 1 calc R . . C12 C 0.2311(2) 0.45854(16) 0.92568(10) 0.0418(5) Uani 1 1 d . . . H12 H 0.2154 0.4683 0.8868 0.050 Uiso 1 1 calc R . . C13 C 0.3520(2) 0.51305(16) 0.94189(9) 0.0396(5) Uani 1 1 d . . . H13 H 0.3704 0.4951 0.9796 0.048 Uiso 1 1 calc R . . C14 C 0.4664(2) 0.47483(16) 0.90698(10) 0.0409(5) Uani 1 1 d . . . C15 C 0.5712(2) 0.54756(18) 0.92504(12) 0.0524(7) Uani 1 1 d . . . H15A H 0.6042 0.5306 0.9607 0.063 Uiso 1 1 calc R . . H15B H 0.6418 0.5483 0.8993 0.063 Uiso 1 1 calc R . . C16 C 0.5033(3) 0.64638(18) 0.92644(12) 0.0544(7) Uani 1 1 d . . . H16A H 0.5120 0.6792 0.8917 0.065 Uiso 1 1 calc R . . H16B H 0.5401 0.6875 0.9545 0.065 Uiso 1 1 calc R . . C17 C 0.3594(2) 0.62544(16) 0.93884(10) 0.0454(6) Uani 1 1 d . . . H17 H 0.3101 0.6457 0.9069 0.054 Uiso 1 1 calc R . . C18 C 0.5356(2) 0.35080(18) 0.97881(10) 0.0481(6) Uani 1 1 d . . . H18A H 0.6076 0.3927 0.9857 0.072 Uiso 1 1 calc R . . H18B H 0.5603 0.2843 0.9848 0.072 Uiso 1 1 calc R . . H18C H 0.4665 0.3675 1.0029 0.072 Uiso 1 1 calc R . . C19 C 0.3911(3) 0.15393(18) 0.96574(10) 0.0474(6) Uani 1 1 d . . . H19A H 0.3554 0.0896 0.9681 0.071 Uiso 1 1 calc R . . H19B H 0.3481 0.1960 0.9910 0.071 Uiso 1 1 calc R . . H19C H 0.4810 0.1516 0.9743 0.071 Uiso 1 1 calc R . . C20 C 0.3084(3) 0.68508(17) 0.98786(11) 0.0490(6) Uani 1 1 d . . . C21 C 0.3293(3) 0.79406(18) 0.97646(13) 0.0668(8) Uani 1 1 d . . . H21A H 0.2833 0.8320 1.0029 0.100 Uiso 1 1 calc R . . H21B H 0.2983 0.8094 0.9407 0.100 Uiso 1 1 calc R . . H21C H 0.4192 0.8089 0.9787 0.100 Uiso 1 1 calc R . . C22 C 0.3684(3) 0.6541(2) 1.04163(11) 0.0591(7) Uani 1 1 d . . . H22A H 0.3485 0.5859 1.0477 0.071 Uiso 1 1 calc R . . H22B H 0.4609 0.6597 1.0385 0.071 Uiso 1 1 calc R . . C23 C 0.3254(4) 0.7117(2) 1.09103(12) 0.0696(8) Uani 1 1 d . . . H23A H 0.3564 0.7781 1.0877 0.083 Uiso 1 1 calc R . . H23B H 0.2323 0.7139 1.0916 0.083 Uiso 1 1 calc R . . C24 C 0.3721(3) 0.6701(2) 1.14394(13) 0.0714(8) Uani 1 1 d . . . H24 H 0.4433 0.6293 1.1420 0.086 Uiso 1 1 calc R . . C25 C 0.3242(3) 0.6846(3) 1.19255(13) 0.0744(9) Uani 1 1 d . . . C26 C 0.3781(5) 0.6365(3) 1.24290(16) 0.1073(14) Uani 1 1 d . . . H26A H 0.4503 0.5967 1.2331 0.161 Uiso 1 1 calc R . . H26B H 0.3132 0.5965 1.2593 0.161 Uiso 1 1 calc R . . H26C H 0.4050 0.6856 1.2682 0.161 Uiso 1 1 calc R . . C27 C 0.2096(4) 0.7463(3) 1.20297(16) 0.1107(14) Uani 1 1 d . . . H27A H 0.1704 0.7637 1.1690 0.166 Uiso 1 1 calc R . . H27B H 0.2353 0.8043 1.2219 0.166 Uiso 1 1 calc R . . H27C H 0.1492 0.7108 1.2248 0.166 Uiso 1 1 calc R . . C28 C 0.5469(3) -0.01130(19) 0.89897(12) 0.0579(7) Uani 1 1 d . . . H28A H 0.5674 -0.0751 0.8855 0.087 Uiso 1 1 calc R . . H28B H 0.4848 -0.0167 0.9277 0.087 Uiso 1 1 calc R . . H28C H 0.6233 0.0191 0.9127 0.087 Uiso 1 1 calc R . . C29 C 0.5729(3) 0.0325(2) 0.80180(12) 0.0661(8) Uani 1 1 d . . . H29A H 0.5556 0.0823 0.7754 0.099 Uiso 1 1 calc R . . H29B H 0.5521 -0.0301 0.7868 0.099 Uiso 1 1 calc R . . H29C H 0.6622 0.0341 0.8114 0.099 Uiso 1 1 calc R . . C30 C 0.4438(3) 0.49460(18) 0.84597(10) 0.0502(6) Uani 1 1 d . . . H30A H 0.5247 0.4949 0.8273 0.075 Uiso 1 1 calc R . . H30B H 0.4027 0.5567 0.8416 0.075 Uiso 1 1 calc R . . H30C H 0.3900 0.4444 0.8311 0.075 Uiso 1 1 calc R . . C31 C 0.2923(4) -0.1280(2) 0.79019(14) 0.0711(9) Uani 1 1 d . . . C32 C 0.2997(4) -0.2361(2) 0.79228(16) 0.0928(11) Uani 1 1 d . A . H32A H 0.2915 -0.2620 0.7562 0.139 Uiso 1 1 calc R . . H32B H 0.2314 -0.2607 0.8146 0.139 Uiso 1 1 calc R . . H32C H 0.3808 -0.2553 0.8074 0.139 Uiso 1 1 calc R . . C33 C 0.8280(3) 0.1765(3) 0.86551(14) 0.0764(9) Uani 1 1 d . . . C34 C 0.9194(3) 0.1477(3) 0.82159(17) 0.1024(14) Uani 1 1 d . B . H34A H 1.0059 0.1545 0.8345 0.154 Uiso 1 1 calc R . . H34B H 0.9069 0.1890 0.7905 0.154 Uiso 1 1 calc R . . H34C H 0.9041 0.0811 0.8115 0.154 Uiso 1 1 calc R . . C35 C 0.0034(3) 0.4922(3) 0.92635(13) 0.0741(8) Uani 1 1 d DU D . H35A H -0.0649 0.5112 0.9510 0.089 Uiso 1 1 calc R . . H35B H -0.0139 0.4258 0.9149 0.089 Uiso 1 1 calc RD . . C36 C -0.0027(4) 0.5542(4) 0.87918(16) 0.1036(12) Uani 1 1 d DU . . H36 H 0.0324 0.6157 0.8848 0.124 Uiso 0.60 1 calc PR C 1 H36' H 0.0243 0.6203 0.8737 0.124 Uiso 0.40 1 d PR C 2 C37 C -0.0465(8) 0.5416(6) 0.8313(3) 0.120(2) Uani 0.70 1 d PU D 1 H37A H -0.0835 0.4824 0.8217 0.144 Uiso 0.60 1 calc PR D 1 H37B H -0.0414 0.5917 0.8059 0.144 Uiso 0.60 1 calc PR D 1 C37' C -0.0635(16) 0.4785(12) 0.8423(5) 0.115(4) Uani 0.30 1 d PDU D 2 H37C H -0.0855 0.4948 0.8068 0.138 Uiso 0.40 1 calc PR D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0736(13) 0.0419(10) 0.0583(11) -0.0073(8) -0.0162(9) 0.0026(9) O3 0.0336(9) 0.0688(12) 0.0476(9) -0.0050(8) -0.0004(7) 0.0095(8) O2 0.159(10) 0.069(3) 0.069(5) -0.006(4) -0.049(4) 0.008(5) O4 0.062(3) 0.134(5) 0.069(3) -0.025(4) -0.025(2) 0.025(4) O2' 0.100(9) 0.099(6) 0.082(9) -0.008(7) -0.048(6) 0.007(6) O4' 0.070(6) 0.194(12) 0.076(5) -0.010(9) -0.026(4) 0.059(9) O5 0.0362(8) 0.0493(10) 0.0628(10) -0.0085(8) 0.0093(7) 0.0021(7) O6 0.0467(11) 0.0533(11) 0.0794(13) -0.0171(10) 0.0048(9) -0.0001(8) C1 0.0413(14) 0.0437(13) 0.0609(16) 0.0005(12) -0.0019(12) -0.0002(11) C2 0.0480(16) 0.0472(14) 0.0736(19) -0.0032(13) -0.0046(14) -0.0024(12) C3 0.0604(17) 0.0436(14) 0.0493(15) 0.0008(11) -0.0099(12) 0.0021(12) C4 0.0494(15) 0.0487(15) 0.0453(14) -0.0033(11) -0.0019(12) 0.0024(12) C5 0.0395(13) 0.0438(13) 0.0374(12) 0.0012(10) -0.0029(10) 0.0038(10) C6 0.0346(13) 0.0523(14) 0.0385(13) -0.0039(10) 0.0019(10) 0.0063(10) C7 0.0333(13) 0.0550(14) 0.0447(14) -0.0013(11) 0.0023(10) -0.0030(11) C8 0.0322(12) 0.0450(13) 0.0386(12) -0.0026(10) 0.0005(10) -0.0035(10) C9 0.0357(12) 0.0410(12) 0.0394(12) 0.0003(10) -0.0022(10) 0.0000(10) C10 0.0341(12) 0.0406(12) 0.0461(13) 0.0018(10) 0.0004(10) -0.0003(10) C11 0.0348(13) 0.0442(13) 0.0521(14) -0.0027(11) 0.0028(10) -0.0031(11) C12 0.0350(13) 0.0426(12) 0.0477(14) -0.0029(10) 0.0049(10) -0.0013(10) C13 0.0376(13) 0.0408(13) 0.0405(12) -0.0010(10) 0.0041(10) -0.0027(10) C14 0.0370(13) 0.0439(13) 0.0416(13) 0.0008(10) 0.0037(10) -0.0032(10) C15 0.0433(15) 0.0511(15) 0.0629(17) -0.0048(12) 0.0068(12) -0.0114(12) C16 0.0519(16) 0.0494(15) 0.0620(16) -0.0044(12) 0.0110(13) -0.0130(12) C17 0.0451(14) 0.0429(13) 0.0482(14) -0.0006(10) 0.0012(11) -0.0045(11) C18 0.0438(14) 0.0531(14) 0.0474(14) -0.0016(12) -0.0046(11) -0.0009(11) C19 0.0486(15) 0.0458(13) 0.0479(14) 0.0050(11) 0.0016(11) 0.0036(11) C20 0.0462(15) 0.0426(13) 0.0583(15) -0.0043(11) 0.0021(12) -0.0021(11) C21 0.076(2) 0.0476(16) 0.077(2) -0.0062(13) 0.0042(16) -0.0046(14) C22 0.0624(17) 0.0543(15) 0.0605(17) -0.0078(13) -0.0011(14) -0.0024(13) C23 0.090(2) 0.0599(17) 0.0585(18) -0.0138(14) -0.0050(17) 0.0056(15) C24 0.078(2) 0.0710(19) 0.066(2) -0.0128(16) -0.0070(16) 0.0064(16) C25 0.076(2) 0.085(2) 0.062(2) -0.0121(17) -0.0077(17) -0.0055(18) C26 0.118(3) 0.135(4) 0.069(2) 0.002(2) -0.015(2) -0.002(3) C27 0.107(3) 0.146(4) 0.079(3) -0.021(3) 0.006(2) 0.027(3) C28 0.0579(16) 0.0501(15) 0.0657(18) 0.0000(13) -0.0081(13) 0.0105(12) C29 0.0707(19) 0.0586(17) 0.0690(19) -0.0213(15) 0.0096(15) 0.0010(14) C30 0.0555(16) 0.0499(15) 0.0451(15) 0.0020(11) 0.0075(12) 0.0007(12) C31 0.086(2) 0.0580(19) 0.069(2) -0.0093(15) -0.0204(18) -0.0015(17) C32 0.125(3) 0.0585(19) 0.094(3) -0.0207(18) -0.023(2) -0.010(2) C33 0.0404(17) 0.120(3) 0.069(2) -0.008(2) -0.0052(15) 0.0176(18) C34 0.0438(19) 0.160(4) 0.103(3) -0.027(3) 0.0073(17) 0.021(2) C35 0.0384(13) 0.102(2) 0.0822(19) 0.0046(15) 0.0039(12) 0.0192(16) C36 0.080(2) 0.143(3) 0.087(2) 0.0189(18) -0.0043(17) 0.034(2) C37 0.118(5) 0.157(6) 0.085(2) 0.007(3) -0.009(3) 0.056(5) C37' 0.091(8) 0.167(8) 0.088(5) 0.012(6) -0.017(6) 0.029(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C31 1.325(3) . ? O1 C3 1.464(3) . ? O3 C33 1.323(3) . ? O3 C6 1.455(3) . ? O2 C31 1.217(11) . ? O4 C33 1.229(9) . ? O2' C31 1.239(17) . ? O4' C33 1.231(14) . ? O5 C35 1.430(3) . ? O5 C12 1.440(3) . ? O6 C20 1.434(3) . ? O6 H6 0.8200 . ? C1 C2 1.531(4) . ? C1 C10 1.536(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.499(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.535(4) . ? C3 H3 0.9800 . ? C4 C29 1.535(4) . ? C4 C28 1.534(4) . ? C4 C5 1.578(3) . ? C5 C6 1.536(3) . ? C5 C10 1.581(3) . ? C5 H5 0.9800 . ? C6 C7 1.525(3) . ? C6 H6A 0.9800 . ? C7 C8 1.528(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C18 1.552(3) . ? C8 C9 1.563(3) . ? C8 C14 1.575(3) . ? C9 C11 1.541(3) . ? C9 C10 1.567(3) . ? C9 H9 0.9800 . ? C10 C19 1.541(3) . ? C11 C12 1.518(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.517(3) . ? C12 H12 0.9800 . ? C13 C17 1.546(3) . ? C13 C14 1.560(3) . ? C13 H13 0.9800 . ? C14 C30 1.543(3) . ? C14 C15 1.545(3) . ? C15 C16 1.530(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.556(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.551(3) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C22 1.523(4) . ? C20 C21 1.537(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.517(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.502(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.311(4) . ? C24 H24 0.9300 . ? C25 C27 1.485(5) . ? C25 C26 1.512(5) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C32 1.487(4) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.493(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.440(5) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.276(7) . ? C36 C37' 1.517(13) . ? C36 H36 0.9300 . ? C36 H36' 0.9600 . ? C37 H37A 0.9300 . ? C37 H37B 0.9300 . ? C37' H37C 0.9300 . ? C37' H37D 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 O1 C3 118.8(2) . . ? C33 O3 C6 118.5(2) . . ? C35 O5 C12 114.67(19) . . ? C20 O6 H6 109.5 . . ? C2 C1 C10 113.22(19) . . ? C2 C1 H1A 108.9 . . ? C10 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? C10 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 109.8(2) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C2 107.8(2) . . ? O1 C3 C4 107.4(2) . . ? C2 C3 C4 116.7(2) . . ? O1 C3 H3 108.2 . . ? C2 C3 H3 108.2 . . ? C4 C3 H3 108.2 . . ? C29 C4 C3 105.1(2) . . ? C29 C4 C28 107.8(2) . . ? C3 C4 C28 111.9(2) . . ? C29 C4 C5 111.3(2) . . ? C3 C4 C5 106.57(19) . . ? C28 C4 C5 113.8(2) . . ? C6 C5 C4 116.26(19) . . ? C6 C5 C10 108.22(18) . . ? C4 C5 C10 116.06(18) . . ? C6 C5 H5 105.0 . . ? C4 C5 H5 105.0 . . ? C10 C5 H5 105.0 . . ? O3 C6 C7 106.02(18) . . ? O3 C6 C5 109.75(18) . . ? C7 C6 C5 111.60(19) . . ? O3 C6 H6A 109.8 . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C6 C7 C8 113.84(19) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C18 107.62(19) . . ? C7 C8 C9 107.58(18) . . ? C18 C8 C9 113.30(19) . . ? C7 C8 C14 111.16(19) . . ? C18 C8 C14 109.75(18) . . ? C9 C8 C14 107.45(17) . . ? C11 C9 C8 111.38(18) . . ? C11 C9 C10 114.35(18) . . ? C8 C9 C10 115.94(18) . . ? C11 C9 H9 104.6 . . ? C8 C9 H9 104.6 . . ? C10 C9 H9 104.6 . . ? C1 C10 C19 107.16(19) . . ? C1 C10 C9 107.83(18) . . ? C19 C10 C9 112.81(19) . . ? C1 C10 C5 107.53(19) . . ? C19 C10 C5 114.45(18) . . ? C9 C10 C5 106.77(18) . . ? C12 C11 C9 112.54(19) . . ? C12 C11 H11A 109.1 . . ? C9 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C9 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? O5 C12 C13 111.14(18) . . ? O5 C12 C11 108.90(18) . . ? C13 C12 C11 109.41(19) . . ? O5 C12 H12 109.1 . . ? C13 C12 H12 109.1 . . ? C11 C12 H12 109.1 . . ? C12 C13 C17 121.4(2) . . ? C12 C13 C14 108.85(18) . . ? C17 C13 C14 105.69(18) . . ? C12 C13 H13 106.7 . . ? C17 C13 H13 106.7 . . ? C14 C13 H13 106.7 . . ? C30 C14 C15 105.9(2) . . ? C30 C14 C13 111.1(2) . . ? C15 C14 C13 99.45(18) . . ? C30 C14 C8 112.24(19) . . ? C15 C14 C8 117.1(2) . . ? C13 C14 C8 110.30(18) . . ? C16 C15 C14 104.6(2) . . ? C16 C15 H15A 110.8 . . ? C14 C15 H15A 110.8 . . ? C16 C15 H15B 110.8 . . ? C14 C15 H15B 110.8 . . ? H15A C15 H15B 108.9 . . ? C15 C16 C17 106.61(19) . . ? C15 C16 H16A 110.4 . . ? C17 C16 H16A 110.4 . . ? C15 C16 H16B 110.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C13 C17 C20 118.1(2) . . ? C13 C17 C16 104.01(19) . . ? C20 C17 C16 112.6(2) . . ? C13 C17 H17 107.2 . . ? C20 C17 H17 107.2 . . ? C16 C17 H17 107.2 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O6 C20 C22 108.9(2) . . ? O6 C20 C21 103.9(2) . . ? C22 C20 C21 111.8(2) . . ? O6 C20 C17 110.1(2) . . ? C22 C20 C17 112.8(2) . . ? C21 C20 C17 108.9(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C20 115.4(2) . . ? C23 C22 H22A 108.4 . . ? C20 C22 H22A 108.4 . . ? C23 C22 H22B 108.4 . . ? C20 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? C24 C23 C22 113.6(3) . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23B 108.8 . . ? C22 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C25 C24 C23 127.5(3) . . ? C25 C24 H24 116.2 . . ? C23 C24 H24 116.2 . . ? C24 C25 C27 123.4(3) . . ? C24 C25 C26 122.7(3) . . ? C27 C25 C26 114.0(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C4 C28 H28A 109.5 . . ? C4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C14 C30 H30A 109.5 . . ? C14 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C14 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O2 C31 O2' 33.3(7) . . ? O2 C31 O1 124.1(6) . . ? O2' C31 O1 117.5(8) . . ? O2 C31 C32 123.5(6) . . ? O2' C31 C32 125.6(9) . . ? O1 C31 C32 111.1(3) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O4 C33 O4' 39.0(6) . . ? O4 C33 O3 121.7(5) . . ? O4' C33 O3 121.7(7) . . ? O4 C33 C34 124.9(5) . . ? O4' C33 C34 119.7(7) . . ? O3 C33 C34 111.2(3) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O5 C35 C36 116.4(3) . . ? O5 C35 H35A 108.2 . . ? C36 C35 H35A 108.2 . . ? O5 C35 H35B 108.2 . . ? C36 C35 H35B 108.2 . . ? H35A C35 H35B 107.3 . . ? C37 C36 C35 132.9(6) . . ? C37 C36 C37' 37.4(6) . . ? C35 C36 C37' 95.5(7) . . ? C37 C36 H36 113.6 . . ? C35 C36 H36 113.6 . . ? C37' C36 H36 150.9 . . ? C37 C36 H36' 95.9 . . ? C35 C36 H36' 131.2 . . ? C37' C36 H36' 133.3 . . ? H36 C36 H36' 17.7 . . ? C36 C37 H37A 120.0 . . ? C36 C37 H37B 120.0 . . ? H37A C37 H37B 120.0 . . ? C36 C37' H37C 120.0 . . ? C36 C37' H37D 120.0 . . ? H37C C37' H37D 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -57.7(3) . . . . ? C31 O1 C3 C2 93.6(3) . . . . ? C31 O1 C3 C4 -139.8(3) . . . . ? C1 C2 C3 O1 178.0(2) . . . . ? C1 C2 C3 C4 57.1(3) . . . . ? O1 C3 C4 C29 68.5(3) . . . . ? C2 C3 C4 C29 -170.5(2) . . . . ? O1 C3 C4 C28 -48.3(3) . . . . ? C2 C3 C4 C28 72.8(3) . . . . ? O1 C3 C4 C5 -173.23(18) . . . . ? C2 C3 C4 C5 -52.2(3) . . . . ? C29 C4 C5 C6 -66.6(3) . . . . ? C3 C4 C5 C6 179.3(2) . . . . ? C28 C4 C5 C6 55.4(3) . . . . ? C29 C4 C5 C10 164.4(2) . . . . ? C3 C4 C5 C10 50.3(3) . . . . ? C28 C4 C5 C10 -73.5(3) . . . . ? C33 O3 C6 C7 93.9(3) . . . . ? C33 O3 C6 C5 -145.4(3) . . . . ? C4 C5 C6 O3 48.5(3) . . . . ? C10 C5 C6 O3 -178.86(17) . . . . ? C4 C5 C6 C7 165.68(19) . . . . ? C10 C5 C6 C7 -61.6(2) . . . . ? O3 C6 C7 C8 178.87(18) . . . . ? C5 C6 C7 C8 59.4(3) . . . . ? C6 C7 C8 C18 71.0(2) . . . . ? C6 C7 C8 C9 -51.4(3) . . . . ? C6 C7 C8 C14 -168.79(19) . . . . ? C7 C8 C9 C11 -174.32(19) . . . . ? C18 C8 C9 C11 66.9(2) . . . . ? C14 C8 C9 C11 -54.5(2) . . . . ? C7 C8 C9 C10 52.6(3) . . . . ? C18 C8 C9 C10 -66.2(3) . . . . ? C14 C8 C9 C10 172.39(19) . . . . ? C2 C1 C10 C19 -68.4(3) . . . . ? C2 C1 C10 C9 169.9(2) . . . . ? C2 C1 C10 C5 55.1(3) . . . . ? C11 C9 C10 C1 55.7(3) . . . . ? C8 C9 C10 C1 -172.58(19) . . . . ? C11 C9 C10 C19 -62.4(3) . . . . ? C8 C9 C10 C19 69.3(2) . . . . ? C11 C9 C10 C5 171.03(18) . . . . ? C8 C9 C10 C5 -57.3(2) . . . . ? C6 C5 C10 C1 174.1(2) . . . . ? C4 C5 C10 C1 -53.1(3) . . . . ? C6 C5 C10 C19 -67.0(2) . . . . ? C4 C5 C10 C19 65.8(3) . . . . ? C6 C5 C10 C9 58.6(2) . . . . ? C4 C5 C10 C9 -168.58(18) . . . . ? C8 C9 C11 C12 56.1(3) . . . . ? C10 C9 C11 C12 -170.07(19) . . . . ? C35 O5 C12 C13 145.6(2) . . . . ? C35 O5 C12 C11 -93.8(3) . . . . ? C9 C11 C12 O5 179.86(18) . . . . ? C9 C11 C12 C13 -58.5(3) . . . . ? O5 C12 C13 C17 -55.8(3) . . . . ? C11 C12 C13 C17 -176.1(2) . . . . ? O5 C12 C13 C14 -178.70(18) . . . . ? C11 C12 C13 C14 61.0(2) . . . . ? C12 C13 C14 C30 62.2(2) . . . . ? C17 C13 C14 C30 -69.7(2) . . . . ? C12 C13 C14 C15 173.43(19) . . . . ? C17 C13 C14 C15 41.6(2) . . . . ? C12 C13 C14 C8 -62.9(2) . . . . ? C17 C13 C14 C8 165.22(18) . . . . ? C7 C8 C14 C30 51.6(2) . . . . ? C18 C8 C14 C30 170.5(2) . . . . ? C9 C8 C14 C30 -65.9(2) . . . . ? C7 C8 C14 C15 -71.2(3) . . . . ? C18 C8 C14 C15 47.7(3) . . . . ? C9 C8 C14 C15 171.3(2) . . . . ? C7 C8 C14 C13 176.04(19) . . . . ? C18 C8 C14 C13 -65.0(2) . . . . ? C9 C8 C14 C13 58.6(2) . . . . ? C30 C14 C15 C16 72.9(2) . . . . ? C13 C14 C15 C16 -42.4(2) . . . . ? C8 C14 C15 C16 -161.1(2) . . . . ? C14 C15 C16 C17 28.4(3) . . . . ? C12 C13 C17 C20 85.1(3) . . . . ? C14 C13 C17 C20 -150.6(2) . . . . ? C12 C13 C17 C16 -149.3(2) . . . . ? C14 C13 C17 C16 -24.9(3) . . . . ? C15 C16 C17 C13 -2.0(3) . . . . ? C15 C16 C17 C20 127.1(2) . . . . ? C13 C17 C20 O6 -68.3(3) . . . . ? C16 C17 C20 O6 170.3(2) . . . . ? C13 C17 C20 C22 53.6(3) . . . . ? C16 C17 C20 C22 -67.8(3) . . . . ? C13 C17 C20 C21 178.3(2) . . . . ? C16 C17 C20 C21 57.0(3) . . . . ? O6 C20 C22 C23 -59.2(3) . . . . ? C21 C20 C22 C23 55.2(3) . . . . ? C17 C20 C22 C23 178.3(2) . . . . ? C20 C22 C23 C24 171.9(3) . . . . ? C22 C23 C24 C25 -158.9(3) . . . . ? C23 C24 C25 C27 0.9(6) . . . . ? C23 C24 C25 C26 178.5(3) . . . . ? C3 O1 C31 O2 16.5(7) . . . . ? C3 O1 C31 O2' -21.7(9) . . . . ? C3 O1 C31 C32 -176.4(3) . . . . ? C6 O3 C33 O4 -17.9(7) . . . . ? C6 O3 C33 O4' 28.3(9) . . . . ? C6 O3 C33 C34 178.2(3) . . . . ? C12 O5 C35 C36 -62.6(4) . . . . ? O5 C35 C36 C37 136.5(6) . . . . ? O5 C35 C36 C37' 134.4(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O5 0.82 1.90 2.711(2) 169.4 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 847812' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_018 #TrackingRef '068101 (1).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H58 O7, C2 H4 O2' _chemical_formula_sum 'C38 H62 O9' _chemical_formula_weight 662.88 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.7254(17) _cell_length_b 9.5176(19) _cell_length_c 12.415(3) _cell_angle_alpha 89.65(3) _cell_angle_beta 80.46(3) _cell_angle_gamma 70.65(3) _cell_volume 958.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2958 _cell_measurement_theta_min 3.61 _cell_measurement_theta_max 67.51 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8603 _exptl_absorpt_correction_T_max 0.9323 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4282 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 67.51 _reflns_number_total 2958 _reflns_number_gt 2899 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1018P)^2^+0.1460P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0108(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(3) _refine_ls_number_reflns 2958 _refine_ls_number_parameters 425 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9150(4) 1.1126(3) -0.3172(2) 0.0631(8) Uani 1 1 d . . . O2 O 1.0228(6) 0.9063(6) -0.4257(4) 0.1048(16) Uani 1 1 d . . . O3 O 0.2966(3) 1.2481(3) -0.1115(2) 0.0499(7) Uani 1 1 d . . . O4 O 0.1887(5) 1.4362(4) 0.0169(3) 0.0809(11) Uani 1 1 d . . . O5 O 0.6919(3) 0.5342(2) 0.20693(17) 0.0394(5) Uani 1 1 d . . . O6 O 0.8508(4) 0.3916(3) 0.0595(2) 0.0616(8) Uani 1 1 d . . . O7 O 0.4764(4) 0.4022(3) 0.3178(2) 0.0574(7) Uani 1 1 d . . . H7A H 0.4632 0.3357 0.3566 0.086 Uiso 1 1 calc R . . O8 O 0.5085(5) 0.1458(4) 0.4200(3) 0.0805(10) Uani 1 1 d . . . H8A H 0.4541 0.1077 0.3898 0.121 Uiso 1 1 calc R . . C1 C 0.8446(4) 0.8756(4) -0.0828(3) 0.0456(8) Uani 1 1 d . . . H1A H 0.9143 0.8264 -0.0310 0.055 Uiso 1 1 calc R . . H1B H 0.8274 0.7989 -0.1256 0.055 Uiso 1 1 calc R . . C1' C 0.6590(7) 0.0540(6) 0.4109(4) 0.0718(13) Uani 1 1 d . . . C2 C 0.9339(5) 0.9609(5) -0.1591(3) 0.0545(10) Uani 1 1 d . . . H2A H 0.9576 1.0344 -0.1170 0.065 Uiso 1 1 calc R . . H2B H 1.0375 0.8926 -0.1977 0.065 Uiso 1 1 calc R . . C2' C 0.6770(9) -0.0949(6) 0.4529(5) 0.0915(18) Uani 1 1 d . . . H2'A H 0.7919 -0.1537 0.4433 0.137 Uiso 1 1 calc R . . H2'B H 0.6209 -0.1431 0.4134 0.137 Uiso 1 1 calc R . . H2'C H 0.6300 -0.0848 0.5292 0.137 Uiso 1 1 calc R . . C3 C 0.8253(5) 1.0378(4) -0.2404(3) 0.0489(9) Uani 1 1 d . . . H3A H 0.8039 0.9610 -0.2818 0.059 Uiso 1 1 calc R . . C4 C 0.6583(5) 1.1528(4) -0.1898(3) 0.0412(8) Uani 1 1 d . . . C5 C 0.5721(4) 1.0677(3) -0.1037(2) 0.0350(7) Uani 1 1 d . . . H5A H 0.5517 0.9926 -0.1476 0.042 Uiso 1 1 calc R . . C6 C 0.4010(4) 1.1585(4) -0.0391(3) 0.0389(7) Uani 1 1 d . . . H6A H 0.4128 1.2229 0.0180 0.047 Uiso 1 1 calc R . . C7 C 0.3099(4) 1.0573(4) 0.0115(3) 0.0402(8) Uani 1 1 d . . . H7B H 0.2921 0.9998 -0.0465 0.048 Uiso 1 1 calc R . . H7C H 0.2026 1.1184 0.0504 0.048 Uiso 1 1 calc R . . C8 C 0.4007(4) 0.9489(3) 0.0913(2) 0.0346(7) Uani 1 1 d . . . C9 C 0.5830(4) 0.8710(3) 0.0332(2) 0.0340(7) Uani 1 1 d . . . H9A H 0.5742 0.8135 -0.0293 0.041 Uiso 1 1 calc R . . C10 C 0.6756(4) 0.9760(3) -0.0187(2) 0.0358(7) Uani 1 1 d . . . C11 C 0.6788(4) 0.7524(4) 0.1050(3) 0.0384(7) Uani 1 1 d . . . H11A H 0.7898 0.7026 0.0658 0.046 Uiso 1 1 calc R . . H11B H 0.6870 0.8010 0.1712 0.046 Uiso 1 1 calc R . . C12 C 0.5947(4) 0.6367(3) 0.1355(2) 0.0368(7) Uani 1 1 d . . . H12A H 0.5933 0.5818 0.0693 0.044 Uiso 1 1 calc R . . C13 C 0.4189(4) 0.7117(4) 0.1959(2) 0.0364(7) Uani 1 1 d . . . H13A H 0.4242 0.7701 0.2591 0.044 Uiso 1 1 calc R . . C14 C 0.3221(4) 0.8229(4) 0.1177(3) 0.0381(7) Uani 1 1 d . . . C15 C 0.1457(5) 0.8754(5) 0.1876(4) 0.0540(10) Uani 1 1 d . . . H15A H 0.1333 0.9540 0.2411 0.065 Uiso 1 1 calc R . . H15B H 0.0627 0.9119 0.1415 0.065 Uiso 1 1 calc R . . C16 C 0.1303(5) 0.7355(5) 0.2443(4) 0.0643(12) Uani 1 1 d . . . H16A H 0.0619 0.6947 0.2090 0.077 Uiso 1 1 calc R . . H16B H 0.0793 0.7607 0.3204 0.077 Uiso 1 1 calc R . . C17 C 0.3057(4) 0.6193(4) 0.2361(3) 0.0449(8) Uani 1 1 d . . . H17A H 0.3200 0.5451 0.1776 0.054 Uiso 1 1 calc R . . C18 C 0.3899(5) 1.0400(4) 0.1968(3) 0.0447(8) Uani 1 1 d . . . H18A H 0.4378 1.1164 0.1788 0.067 Uiso 1 1 calc R . . H18B H 0.4489 0.9751 0.2468 0.067 Uiso 1 1 calc R . . H18C H 0.2765 1.0851 0.2303 0.067 Uiso 1 1 calc R . . C19 C 0.7139(5) 1.0726(4) 0.0664(3) 0.0485(8) Uani 1 1 d . . . H19A H 0.7769 1.0089 0.1152 0.073 Uiso 1 1 calc R . . H19B H 0.6124 1.1382 0.1074 0.073 Uiso 1 1 calc R . . H19C H 0.7761 1.1304 0.0292 0.073 Uiso 1 1 calc R . . C20 C 0.3312(5) 0.5360(4) 0.3428(3) 0.0467(8) Uani 1 1 d . . . C21 C 0.1902(7) 0.4732(7) 0.3766(5) 0.0797(15) Uani 1 1 d . . . H21A H 0.2051 0.4215 0.4427 0.120 Uiso 1 1 calc R . . H21B H 0.1908 0.4053 0.3195 0.120 Uiso 1 1 calc R . . H21C H 0.0867 0.5536 0.3886 0.120 Uiso 1 1 calc R . . C22 C 0.3560(6) 0.6279(4) 0.4339(3) 0.0546(9) Uani 1 1 d . . . H22A H 0.2652 0.7218 0.4452 0.065 Uiso 1 1 calc R . . H22B H 0.4565 0.6506 0.4100 0.065 Uiso 1 1 calc R . . C23 C 0.3672(8) 0.5537(6) 0.5441(4) 0.0793(15) Uani 1 1 d . . . H23A H 0.2591 0.5512 0.5765 0.095 Uiso 1 1 calc R . . H23B H 0.4414 0.4515 0.5312 0.095 Uiso 1 1 calc R . . C24 C 0.4270(9) 0.6325(6) 0.6230(4) 0.0820(18) Uani 1 1 d . . . H24A H 0.3468 0.7046 0.6710 0.098 Uiso 1 1 calc R . . C25 C 0.5854(9) 0.6096(5) 0.6318(3) 0.0723(14) Uani 1 1 d . . . C27 C 0.7225(10) 0.4999(8) 0.5625(5) 0.0976(19) Uani 1 1 d . . . H27A H 0.6812 0.4519 0.5119 0.146 Uiso 1 1 calc R . . H27B H 0.7839 0.4268 0.6069 0.146 Uiso 1 1 calc R . . H27C H 0.7931 0.5484 0.5228 0.146 Uiso 1 1 calc R . . C28 C 0.5611(5) 1.1958(5) -0.2859(3) 0.0562(10) Uani 1 1 d . . . H28A H 0.6141 1.2476 -0.3378 0.084 Uiso 1 1 calc R . . H28B H 0.4503 1.2592 -0.2583 0.084 Uiso 1 1 calc R . . H28C H 0.5587 1.1071 -0.3210 0.084 Uiso 1 1 calc R . . C29 C 0.6749(6) 1.2940(4) -0.1408(4) 0.0578(10) Uani 1 1 d . . . H29A H 0.7278 1.3406 -0.1969 0.087 Uiso 1 1 calc R . . H29B H 0.7398 1.2675 -0.0838 0.087 Uiso 1 1 calc R . . H29C H 0.5673 1.3621 -0.1111 0.087 Uiso 1 1 calc R . . C30 C 0.3118(5) 0.7409(4) 0.0139(3) 0.0494(8) Uani 1 1 d . . . H30A H 0.2638 0.6653 0.0343 0.074 Uiso 1 1 calc R . . H30B H 0.4206 0.6956 -0.0276 0.074 Uiso 1 1 calc R . . H30C H 0.2446 0.8109 -0.0297 0.074 Uiso 1 1 calc R . . C31 C 1.0090(6) 1.0310(7) -0.4063(4) 0.0765(15) Uani 1 1 d . . . C32 C 1.0992(9) 1.1173(9) -0.4757(6) 0.117(3) Uani 1 1 d . . . H32A H 1.1660 1.0564 -0.5389 0.176 Uiso 1 1 calc R . . H32B H 1.1685 1.1464 -0.4343 0.176 Uiso 1 1 calc R . . H32C H 1.0212 1.2048 -0.4986 0.176 Uiso 1 1 calc R . . C33 C 0.1964(5) 1.3847(4) -0.0730(4) 0.0581(11) Uani 1 1 d . . . C34 C 0.0930(8) 1.4584(8) -0.1548(6) 0.108(3) Uani 1 1 d . . . H34A H 0.0223 1.5562 -0.1265 0.161 Uiso 1 1 calc R . . H34B H 0.0269 1.4001 -0.1696 0.161 Uiso 1 1 calc R . . H34C H 0.1629 1.4665 -0.2213 0.161 Uiso 1 1 calc R . . C35 C 0.8210(5) 0.4160(4) 0.1559(3) 0.0425(8) Uani 1 1 d . . . C36 C 0.9139(6) 0.3246(5) 0.2355(4) 0.0675(12) Uani 1 1 d . . . H36A H 1.0041 0.2431 0.1973 0.101 Uiso 1 1 calc R . . H36B H 0.8421 0.2862 0.2848 0.101 Uiso 1 1 calc R . . H36C H 0.9558 0.3848 0.2761 0.101 Uiso 1 1 calc R . . C26 C 0.6227(15) 0.6972(9) 0.7163(5) 0.130(4) Uani 1 1 d . . . H26A H 0.5216 0.7653 0.7559 0.195 Uiso 1 1 calc R . . H26B H 0.6902 0.7520 0.6817 0.195 Uiso 1 1 calc R . . H26C H 0.6804 0.6307 0.7660 0.195 Uiso 1 1 calc R . . O9 O 0.7702(8) 0.0895(9) 0.3707(9) 0.202(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0612(18) 0.0667(17) 0.0566(16) 0.0193(13) 0.0077(13) -0.0238(15) O2 0.100(3) 0.096(3) 0.079(3) 0.003(2) 0.032(2) -0.004(2) O3 0.0518(14) 0.0402(13) 0.0439(13) 0.0118(10) -0.0076(11) 0.0023(12) O4 0.074(2) 0.0459(15) 0.115(3) -0.0193(18) -0.0125(19) -0.0109(16) O5 0.0366(12) 0.0375(11) 0.0394(12) 0.0116(9) -0.0079(9) -0.0059(10) O6 0.0586(16) 0.0596(16) 0.0562(17) -0.0073(12) -0.0052(12) -0.0080(14) O7 0.0572(16) 0.0417(13) 0.0663(17) 0.0180(11) -0.0046(12) -0.0102(12) O8 0.091(3) 0.073(2) 0.093(2) 0.0254(17) -0.0282(19) -0.042(2) C1 0.0368(17) 0.0501(19) 0.0490(19) 0.0156(14) -0.0051(14) -0.0147(17) C1' 0.078(3) 0.072(3) 0.064(3) 0.021(2) -0.009(2) -0.025(3) C2 0.042(2) 0.064(2) 0.059(2) 0.0211(18) -0.0047(15) -0.0216(19) C2' 0.116(5) 0.061(3) 0.096(4) 0.024(3) -0.028(3) -0.025(3) C3 0.050(2) 0.052(2) 0.0437(19) 0.0144(15) 0.0008(15) -0.0198(18) C4 0.050(2) 0.0399(16) 0.0347(17) 0.0089(13) -0.0061(13) -0.0166(16) C5 0.0383(16) 0.0330(14) 0.0351(15) 0.0034(11) -0.0090(12) -0.0125(14) C6 0.0417(18) 0.0350(15) 0.0362(16) 0.0055(12) -0.0098(13) -0.0066(15) C7 0.0355(17) 0.0402(17) 0.0415(18) 0.0106(13) -0.0101(13) -0.0066(15) C8 0.0329(16) 0.0357(15) 0.0341(16) 0.0056(12) -0.0087(11) -0.0085(14) C9 0.0326(16) 0.0337(15) 0.0351(16) 0.0053(11) -0.0088(12) -0.0092(14) C10 0.0371(17) 0.0376(16) 0.0358(16) 0.0065(12) -0.0083(12) -0.0156(14) C11 0.0319(16) 0.0391(16) 0.0432(17) 0.0106(12) -0.0092(12) -0.0094(14) C12 0.0374(18) 0.0369(15) 0.0346(16) 0.0071(12) -0.0083(12) -0.0097(14) C13 0.0363(17) 0.0406(16) 0.0339(16) 0.0069(12) -0.0072(12) -0.0145(15) C14 0.0327(17) 0.0415(17) 0.0407(17) 0.0096(13) -0.0103(12) -0.0116(15) C15 0.0335(18) 0.059(2) 0.067(2) 0.0209(18) -0.0059(15) -0.0135(17) C16 0.033(2) 0.075(3) 0.087(3) 0.038(2) -0.0137(18) -0.020(2) C17 0.0355(18) 0.053(2) 0.052(2) 0.0125(15) -0.0112(14) -0.0209(17) C18 0.055(2) 0.0432(17) 0.0352(17) 0.0019(13) -0.0070(13) -0.0154(16) C19 0.059(2) 0.0558(19) 0.0449(19) 0.0095(14) -0.0213(15) -0.0323(18) C20 0.0379(19) 0.0465(18) 0.055(2) 0.0168(15) -0.0031(14) -0.0159(17) C21 0.066(3) 0.089(3) 0.101(4) 0.048(3) -0.020(3) -0.048(3) C22 0.067(2) 0.054(2) 0.0429(19) 0.0166(15) -0.0019(16) -0.0238(19) C23 0.113(4) 0.089(3) 0.049(3) 0.029(2) -0.013(2) -0.052(3) C24 0.129(5) 0.064(3) 0.043(2) 0.0094(19) 0.000(3) -0.026(3) C25 0.121(5) 0.064(3) 0.045(2) 0.0148(18) -0.020(2) -0.046(3) C27 0.129(6) 0.096(4) 0.077(4) 0.010(3) -0.011(3) -0.053(4) C28 0.061(2) 0.063(2) 0.0389(19) 0.0184(16) -0.0083(15) -0.014(2) C29 0.075(3) 0.0427(18) 0.064(2) 0.0092(16) -0.0107(19) -0.0317(19) C30 0.052(2) 0.0555(19) 0.056(2) 0.0164(15) -0.0286(15) -0.0307(18) C31 0.062(3) 0.083(4) 0.064(3) 0.022(2) 0.012(2) -0.007(3) C32 0.088(4) 0.134(6) 0.102(5) 0.033(4) 0.035(4) -0.027(4) C33 0.048(2) 0.0376(19) 0.083(3) 0.0142(18) 0.0014(19) -0.0134(18) C34 0.083(4) 0.088(4) 0.108(4) 0.054(3) -0.002(3) 0.021(3) C35 0.0393(17) 0.0364(16) 0.052(2) 0.0045(13) -0.0043(14) -0.0147(14) C36 0.046(2) 0.058(2) 0.087(3) 0.019(2) -0.018(2) 0.002(2) C26 0.258(12) 0.108(5) 0.068(3) 0.019(3) -0.063(5) -0.103(6) O9 0.101(4) 0.167(6) 0.308(11) 0.151(7) 0.007(5) -0.029(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C31 1.337(6) . ? O1 C3 1.464(4) . ? O2 C31 1.175(8) . ? O3 C33 1.341(5) . ? O3 C6 1.453(4) . ? O4 C33 1.205(6) . ? O5 C35 1.367(4) . ? O5 C12 1.466(4) . ? O6 C35 1.190(5) . ? O7 C20 1.459(5) . ? O7 H7A 0.8200 . ? O8 C1' 1.301(7) . ? O8 H8A 0.8200 . ? C1 C2 1.526(5) . ? C1 C10 1.551(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1' O9 1.166(8) . ? C1' C2' 1.474(8) . ? C2 C3 1.516(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2' H2'A 0.9600 . ? C2' H2'B 0.9600 . ? C2' H2'C 0.9600 . ? C3 C4 1.538(5) . ? C3 H3A 0.9800 . ? C4 C29 1.538(5) . ? C4 C28 1.553(5) . ? C4 C5 1.578(5) . ? C5 C6 1.542(4) . ? C5 C10 1.573(4) . ? C5 H5A 0.9800 . ? C6 C7 1.512(5) . ? C6 H6A 0.9800 . ? C7 C8 1.543(4) . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C8 C18 1.548(4) . ? C8 C9 1.564(4) . ? C8 C14 1.575(5) . ? C9 C11 1.542(4) . ? C9 C10 1.556(4) . ? C9 H9A 0.9800 . ? C10 C19 1.551(4) . ? C11 C12 1.528(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.524(4) . ? C12 H12A 0.9800 . ? C13 C17 1.551(5) . ? C13 C14 1.563(5) . ? C13 H13A 0.9800 . ? C14 C30 1.541(5) . ? C14 C15 1.558(5) . ? C15 C16 1.536(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.550(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.549(5) . ? C17 H17A 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C22 1.520(6) . ? C20 C21 1.536(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.539(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.494(8) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.350(9) . ? C24 H24A 0.9300 . ? C25 C27 1.450(9) . ? C25 C26 1.484(8) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C32 1.494(8) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.488(8) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.475(6) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 O1 C3 116.1(4) . . ? C33 O3 C6 117.2(3) . . ? C35 O5 C12 116.2(3) . . ? C20 O7 H7A 109.5 . . ? C1' O8 H8A 109.5 . . ? C2 C1 C10 113.5(3) . . ? C2 C1 H1A 108.9 . . ? C10 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? C10 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? O9 C1' O8 120.8(6) . . ? O9 C1' C2' 123.5(6) . . ? O8 C1' C2' 115.7(5) . . ? C3 C2 C1 109.0(3) . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C1' C2' H2'A 109.5 . . ? C1' C2' H2'B 109.5 . . ? H2'A C2' H2'B 109.5 . . ? C1' C2' H2'C 109.5 . . ? H2'A C2' H2'C 109.5 . . ? H2'B C2' H2'C 109.5 . . ? O1 C3 C2 108.9(3) . . ? O1 C3 C4 108.4(3) . . ? C2 C3 C4 115.2(3) . . ? O1 C3 H3A 108.0 . . ? C2 C3 H3A 108.0 . . ? C4 C3 H3A 108.0 . . ? C3 C4 C29 113.0(3) . . ? C3 C4 C28 105.1(3) . . ? C29 C4 C28 109.0(3) . . ? C3 C4 C5 106.0(3) . . ? C29 C4 C5 113.5(3) . . ? C28 C4 C5 109.9(3) . . ? C6 C5 C10 106.9(2) . . ? C6 C5 C4 117.0(3) . . ? C10 C5 C4 117.5(3) . . ? C6 C5 H5A 104.6 . . ? C10 C5 H5A 104.6 . . ? C4 C5 H5A 104.6 . . ? O3 C6 C7 104.9(3) . . ? O3 C6 C5 110.7(2) . . ? C7 C6 C5 111.2(3) . . ? O3 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? C6 C7 C8 114.0(3) . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7C 108.8 . . ? C8 C7 H7C 108.8 . . ? H7B C7 H7C 107.6 . . ? C7 C8 C18 108.1(3) . . ? C7 C8 C9 107.8(2) . . ? C18 C8 C9 112.1(3) . . ? C7 C8 C14 110.7(3) . . ? C18 C8 C14 110.9(3) . . ? C9 C8 C14 107.2(2) . . ? C11 C9 C10 115.0(3) . . ? C11 C9 C8 110.9(2) . . ? C10 C9 C8 116.1(2) . . ? C11 C9 H9A 104.5 . . ? C10 C9 H9A 104.5 . . ? C8 C9 H9A 104.5 . . ? C19 C10 C1 106.4(3) . . ? C19 C10 C9 113.8(3) . . ? C1 C10 C9 107.3(3) . . ? C19 C10 C5 114.5(3) . . ? C1 C10 C5 107.9(2) . . ? C9 C10 C5 106.7(3) . . ? C12 C11 C9 111.7(3) . . ? C12 C11 H11A 109.3 . . ? C9 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C9 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? O5 C12 C13 109.8(2) . . ? O5 C12 C11 106.9(3) . . ? C13 C12 C11 110.6(3) . . ? O5 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? C12 C13 C17 121.2(3) . . ? C12 C13 C14 107.8(2) . . ? C17 C13 C14 103.9(3) . . ? C12 C13 H13A 107.8 . . ? C17 C13 H13A 107.8 . . ? C14 C13 H13A 107.8 . . ? C30 C14 C15 106.4(3) . . ? C30 C14 C13 111.4(3) . . ? C15 C14 C13 100.3(3) . . ? C30 C14 C8 112.7(3) . . ? C15 C14 C8 115.4(3) . . ? C13 C14 C8 109.9(3) . . ? C16 C15 C14 104.7(3) . . ? C16 C15 H15A 110.8 . . ? C14 C15 H15A 110.8 . . ? C16 C15 H15B 110.8 . . ? C14 C15 H15B 110.8 . . ? H15A C15 H15B 108.9 . . ? C15 C16 C17 108.3(3) . . ? C15 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? C15 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? C20 C17 C16 112.6(3) . . ? C20 C17 C13 117.9(3) . . ? C16 C17 C13 102.8(3) . . ? C20 C17 H17A 107.7 . . ? C16 C17 H17A 107.7 . . ? C13 C17 H17A 107.7 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O7 C20 C22 108.4(3) . . ? O7 C20 C21 103.1(3) . . ? C22 C20 C21 113.5(4) . . ? O7 C20 C17 108.4(3) . . ? C22 C20 C17 113.8(3) . . ? C21 C20 C17 109.0(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 C23 115.3(4) . . ? C20 C22 H22A 108.5 . . ? C23 C22 H22A 108.5 . . ? C20 C22 H22B 108.5 . . ? C23 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C24 C23 C22 113.1(4) . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? C22 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C23 126.7(5) . . ? C25 C24 H24A 116.7 . . ? C23 C24 H24A 116.7 . . ? C24 C25 C27 122.3(5) . . ? C24 C25 C26 119.5(6) . . ? C27 C25 C26 118.1(7) . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C4 C28 H28A 109.5 . . ? C4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C14 C30 H30A 109.5 . . ? C14 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C14 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O2 C31 O1 124.4(5) . . ? O2 C31 C32 124.5(5) . . ? O1 C31 C32 111.1(5) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O4 C33 O3 123.9(5) . . ? O4 C33 C34 125.7(4) . . ? O3 C33 C34 110.3(5) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O6 C35 O5 123.0(3) . . ? O6 C35 C36 125.6(4) . . ? O5 C35 C36 111.4(3) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -58.7(4) . . . . ? C31 O1 C3 C2 88.7(5) . . . . ? C31 O1 C3 C4 -145.3(4) . . . . ? C1 C2 C3 O1 -176.9(3) . . . . ? C1 C2 C3 C4 61.1(4) . . . . ? O1 C3 C4 C29 -52.3(4) . . . . ? C2 C3 C4 C29 70.0(4) . . . . ? O1 C3 C4 C28 66.4(4) . . . . ? C2 C3 C4 C28 -171.3(4) . . . . ? O1 C3 C4 C5 -177.2(3) . . . . ? C2 C3 C4 C5 -54.9(4) . . . . ? C3 C4 C5 C6 179.3(3) . . . . ? C29 C4 C5 C6 54.8(4) . . . . ? C28 C4 C5 C6 -67.6(4) . . . . ? C3 C4 C5 C10 50.1(3) . . . . ? C29 C4 C5 C10 -74.5(4) . . . . ? C28 C4 C5 C10 163.2(3) . . . . ? C33 O3 C6 C7 97.7(3) . . . . ? C33 O3 C6 C5 -142.2(3) . . . . ? C10 C5 C6 O3 179.6(2) . . . . ? C4 C5 C6 O3 45.4(4) . . . . ? C10 C5 C6 C7 -64.2(3) . . . . ? C4 C5 C6 C7 161.7(3) . . . . ? O3 C6 C7 C8 179.1(2) . . . . ? C5 C6 C7 C8 59.3(3) . . . . ? C6 C7 C8 C18 72.3(3) . . . . ? C6 C7 C8 C9 -49.0(3) . . . . ? C6 C7 C8 C14 -166.1(2) . . . . ? C7 C8 C9 C11 -176.0(3) . . . . ? C18 C8 C9 C11 65.1(3) . . . . ? C14 C8 C9 C11 -56.7(3) . . . . ? C7 C8 C9 C10 50.4(3) . . . . ? C18 C8 C9 C10 -68.5(3) . . . . ? C14 C8 C9 C10 169.7(3) . . . . ? C2 C1 C10 C19 -70.8(4) . . . . ? C2 C1 C10 C9 167.1(3) . . . . ? C2 C1 C10 C5 52.5(4) . . . . ? C11 C9 C10 C19 -62.6(4) . . . . ? C8 C9 C10 C19 69.2(3) . . . . ? C11 C9 C10 C1 54.8(3) . . . . ? C8 C9 C10 C1 -173.4(3) . . . . ? C11 C9 C10 C5 170.2(2) . . . . ? C8 C9 C10 C5 -58.0(3) . . . . ? C6 C5 C10 C19 -65.4(4) . . . . ? C4 C5 C10 C19 68.4(4) . . . . ? C6 C5 C10 C1 176.3(3) . . . . ? C4 C5 C10 C1 -49.8(3) . . . . ? C6 C5 C10 C9 61.4(3) . . . . ? C4 C5 C10 C9 -164.8(2) . . . . ? C10 C9 C11 C12 -169.5(2) . . . . ? C8 C9 C11 C12 56.3(3) . . . . ? C35 O5 C12 C13 152.7(3) . . . . ? C35 O5 C12 C11 -87.3(3) . . . . ? C9 C11 C12 O5 -177.7(2) . . . . ? C9 C11 C12 C13 -58.2(3) . . . . ? O5 C12 C13 C17 -62.3(4) . . . . ? C11 C12 C13 C17 179.9(3) . . . . ? O5 C12 C13 C14 178.4(2) . . . . ? C11 C12 C13 C14 60.6(3) . . . . ? C12 C13 C14 C30 62.4(4) . . . . ? C17 C13 C14 C30 -67.4(3) . . . . ? C12 C13 C14 C15 174.7(3) . . . . ? C17 C13 C14 C15 45.0(3) . . . . ? C12 C13 C14 C8 -63.3(3) . . . . ? C17 C13 C14 C8 166.9(2) . . . . ? C7 C8 C14 C30 53.4(4) . . . . ? C18 C8 C14 C30 173.4(3) . . . . ? C9 C8 C14 C30 -64.0(3) . . . . ? C7 C8 C14 C15 -69.1(4) . . . . ? C18 C8 C14 C15 50.9(4) . . . . ? C9 C8 C14 C15 173.5(3) . . . . ? C7 C8 C14 C13 178.4(2) . . . . ? C18 C8 C14 C13 -61.7(3) . . . . ? C9 C8 C14 C13 61.0(3) . . . . ? C30 C14 C15 C16 79.2(4) . . . . ? C13 C14 C15 C16 -37.0(4) . . . . ? C8 C14 C15 C16 -155.0(3) . . . . ? C14 C15 C16 C17 16.2(5) . . . . ? C15 C16 C17 C20 139.6(4) . . . . ? C15 C16 C17 C13 11.7(5) . . . . ? C12 C13 C17 C20 79.1(4) . . . . ? C14 C13 C17 C20 -159.8(3) . . . . ? C12 C13 C17 C16 -156.3(3) . . . . ? C14 C13 C17 C16 -35.2(4) . . . . ? C16 C17 C20 O7 163.2(3) . . . . ? C13 C17 C20 O7 -77.2(4) . . . . ? C16 C17 C20 C22 -76.1(4) . . . . ? C13 C17 C20 C22 43.4(4) . . . . ? C16 C17 C20 C21 51.7(5) . . . . ? C13 C17 C20 C21 171.2(4) . . . . ? O7 C20 C22 C23 -64.2(5) . . . . ? C21 C20 C22 C23 49.7(5) . . . . ? C17 C20 C22 C23 175.1(4) . . . . ? C20 C22 C23 C24 167.7(4) . . . . ? C22 C23 C24 C25 -87.6(7) . . . . ? C23 C24 C25 C27 -0.4(8) . . . . ? C23 C24 C25 C26 -179.3(5) . . . . ? C3 O1 C31 O2 0.2(9) . . . . ? C3 O1 C31 C32 -177.6(5) . . . . ? C6 O3 C33 O4 0.1(6) . . . . ? C6 O3 C33 C34 -177.3(4) . . . . ? C12 O5 C35 O6 -3.3(5) . . . . ? C12 O5 C35 C36 177.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7A O8 0.82 1.91 2.696(4) 159.9 . _diffrn_measured_fraction_theta_max 0.749 _diffrn_reflns_theta_full 67.51 _diffrn_measured_fraction_theta_full 0.749 _refine_diff_density_max 0.182 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 860719' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dm12091 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H71 Cl O5 Si' _chemical_formula_weight 707.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.3808(7) _cell_length_b 13.5353(11) _cell_length_c 32.994(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4189.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 8345 _cell_measurement_theta_min 4.514 _cell_measurement_theta_max 53.810 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.265 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.156 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6453 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27407 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8260 _reflns_number_gt 7215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.3395P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 8260 _refine_ls_number_parameters 504 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.70612(6) 0.79751(4) 0.171043(17) 0.04227(14) Uani 1 1 d . . . O1 O 0.22359(16) 0.43240(11) 0.00899(4) 0.0374(3) Uani 1 1 d . . . O2 O 0.39316(12) 0.62668(9) 0.13996(3) 0.0217(3) Uani 1 1 d . B . O3 O 0.58681(15) 0.59323(11) 0.17796(4) 0.0391(3) Uani 1 1 d . B . O4 O -0.24263(12) 0.33019(9) 0.23965(3) 0.0230(3) Uani 1 1 d . . . O5 O -0.30500(15) 0.37035(11) 0.31772(4) 0.0365(3) Uani 1 1 d . B . H5 H -0.2858 0.3476 0.2947 0.055 Uiso 1 1 calc R . . C1 C 0.0322(2) 0.37155(16) 0.10569(5) 0.0327(5) Uani 1 1 d . B . H1A H -0.0124 0.3092 0.1149 0.039 Uiso 1 1 calc R . . H1B H -0.0439 0.4220 0.1036 0.039 Uiso 1 1 calc R . . C2 C 0.0972(3) 0.35521(17) 0.06382(6) 0.0397(5) Uani 1 1 d . . . H2A H 0.1689 0.3017 0.0652 0.048 Uiso 1 1 calc R B . H2B H 0.0217 0.3347 0.0446 0.048 Uiso 1 1 calc R . . C3 C 0.1668(2) 0.44884(16) 0.04883(5) 0.0313(4) Uani 1 1 d . B . H3 H 0.0919 0.5012 0.0469 0.038 Uiso 1 1 calc R . . C4 C 0.2880(2) 0.48778(13) 0.07692(5) 0.0259(4) Uani 1 1 d . . . C5 C 0.22096(19) 0.49893(13) 0.12035(5) 0.0218(4) Uani 1 1 d . B . H5A H 0.1455 0.5506 0.1174 0.026 Uiso 1 1 calc R . . C6 C 0.31997(19) 0.53718(13) 0.15383(5) 0.0213(4) Uani 1 1 d . . . H6 H 0.3907 0.4853 0.1617 0.026 Uiso 1 1 calc R B . C7 C 0.23492(18) 0.57132(13) 0.19099(5) 0.0211(4) Uani 1 1 d . B . H7A H 0.1713 0.6262 0.1829 0.025 Uiso 1 1 calc R . . H7B H 0.3021 0.5972 0.2115 0.025 Uiso 1 1 calc R . . C8 C 0.14432(18) 0.48898(12) 0.21038(5) 0.0195(3) Uani 1 1 d . . . C9 C 0.05507(18) 0.44041(12) 0.17584(5) 0.0206(4) Uani 1 1 d . B . H9 H -0.0071 0.4949 0.1655 0.025 Uiso 1 1 calc R . . C10 C 0.1416(2) 0.40535(13) 0.13765(5) 0.0246(4) Uani 1 1 d . . . C11 C -0.0496(2) 0.36322(13) 0.19262(5) 0.0242(4) Uani 1 1 d . . . H11A H 0.0049 0.3082 0.2049 0.029 Uiso 1 1 calc R B . H11B H -0.1068 0.3359 0.1700 0.029 Uiso 1 1 calc R . . C12 C -0.15033(19) 0.40728(13) 0.22462(5) 0.0225(4) Uani 1 1 d . B . H12 H -0.2093 0.4606 0.2120 0.027 Uiso 1 1 calc R . . C13 C -0.06272(18) 0.45061(13) 0.25913(5) 0.0196(3) Uani 1 1 d . . . H13 H -0.0001 0.3967 0.2697 0.024 Uiso 1 1 calc R B . C14 C 0.03652(19) 0.53350(12) 0.24230(5) 0.0202(4) Uani 1 1 d . B . C15 C 0.1012(2) 0.57234(14) 0.28210(5) 0.0256(4) Uani 1 1 d . . . H15A H 0.1741 0.5263 0.2927 0.031 Uiso 1 1 calc R B . H15B H 0.1450 0.6382 0.2782 0.031 Uiso 1 1 calc R . . C16 C -0.0275(2) 0.57842(13) 0.31079(5) 0.0280(4) Uani 1 1 d . B . H16A H -0.0704 0.6452 0.3098 0.034 Uiso 1 1 calc R . . H16B H 0.0023 0.5647 0.3390 0.034 Uiso 1 1 calc R . . C17 C -0.1379(2) 0.49902(13) 0.29618(5) 0.0243(4) Uani 1 1 d . B . H17 H -0.2231 0.5353 0.2857 0.029 Uiso 1 1 calc R . . C18 C 0.24713(19) 0.41642(14) 0.23130(5) 0.0253(4) Uani 1 1 d . B . H18A H 0.3199 0.3949 0.2119 0.038 Uiso 1 1 calc R . . H18B H 0.1937 0.3589 0.2410 0.038 Uiso 1 1 calc R . . H18C H 0.2932 0.4493 0.2543 0.038 Uiso 1 1 calc R . . C19 C 0.2404(2) 0.31558(13) 0.14671(6) 0.0302(4) Uani 1 1 d . B . H19A H 0.2020 0.2781 0.1697 0.045 Uiso 1 1 calc R . . H19B H 0.3363 0.3393 0.1534 0.045 Uiso 1 1 calc R . . H19C H 0.2452 0.2728 0.1228 0.045 Uiso 1 1 calc R . . C20 C -0.18940(19) 0.43161(13) 0.33135(5) 0.0261(4) Uani 1 1 d . . . C21 C -0.2561(2) 0.49622(16) 0.36451(6) 0.0354(5) Uani 1 1 d . B . H21A H -0.3195 0.5451 0.3521 0.053 Uiso 1 1 calc R . . H21B H -0.1805 0.5303 0.3795 0.053 Uiso 1 1 calc R . . H21C H -0.3109 0.4545 0.3831 0.053 Uiso 1 1 calc R . . C22 C -0.0704(2) 0.36609(13) 0.34787(5) 0.0260(4) Uani 1 1 d . B . H22A H 0.0115 0.4087 0.3551 0.031 Uiso 1 1 calc R . . H22B H -0.0387 0.3212 0.3260 0.031 Uiso 1 1 calc R . . C23 C -0.1095(2) 0.30333(15) 0.38500(6) 0.0323(4) Uani 1 1 d . . . H23A H -0.1276 0.3474 0.4084 0.039 Uiso 1 1 calc R B . H23B H -0.1984 0.2664 0.3793 0.039 Uiso 1 1 calc R . . C24 C 0.0063(2) 0.23175(15) 0.39574(6) 0.0354(5) Uani 1 1 d . B . H24 H 0.0463 0.1963 0.3736 0.043 Uiso 1 1 calc R . . C25 C 0.0605(3) 0.21108(18) 0.43187(7) 0.0494(6) Uani 1 1 d . . . C26 C 0.1795(3) 0.1366(2) 0.43653(9) 0.0717(9) Uani 1 1 d . B . H26A H 0.1984 0.1052 0.4103 0.108 Uiso 1 1 calc R . . H26B H 0.1513 0.0862 0.4563 0.108 Uiso 1 1 calc R . . H26C H 0.2658 0.1702 0.4460 0.108 Uiso 1 1 calc R . . C27 C 0.0106(4) 0.2576(3) 0.47044(7) 0.0856(11) Uani 1 1 d . B . H27A H -0.0362 0.3207 0.4644 0.128 Uiso 1 1 calc R . . H27B H 0.0924 0.2692 0.4883 0.128 Uiso 1 1 calc R . . H27C H -0.0572 0.2134 0.4839 0.128 Uiso 1 1 calc R . . C28 C 0.4195(2) 0.42105(16) 0.07512(6) 0.0349(5) Uani 1 1 d . B . H28A H 0.3917 0.3528 0.0812 0.052 Uiso 1 1 calc R . . H28B H 0.4897 0.4434 0.0951 0.052 Uiso 1 1 calc R . . H28C H 0.4614 0.4242 0.0479 0.052 Uiso 1 1 calc R . . C29 C 0.3300(2) 0.58872(15) 0.05898(5) 0.0314(4) Uani 1 1 d . B . H29A H 0.3400 0.5828 0.0295 0.047 Uiso 1 1 calc R . . H29B H 0.4209 0.6101 0.0707 0.047 Uiso 1 1 calc R . . H29C H 0.2560 0.6374 0.0653 0.047 Uiso 1 1 calc R . . C30 C -0.0516(2) 0.61988(13) 0.22414(5) 0.0259(4) Uani 1 1 d . . . H30A H -0.1344 0.6329 0.2414 0.039 Uiso 1 1 calc R B . H30B H -0.0839 0.6020 0.1969 0.039 Uiso 1 1 calc R . . H30C H 0.0080 0.6793 0.2227 0.039 Uiso 1 1 calc R . . C31 C 0.51961(19) 0.64714(14) 0.15649(5) 0.0238(4) Uani 1 1 d . . . C32 C 0.5609(2) 0.74974(14) 0.14284(6) 0.0275(4) Uani 1 1 d . B . H32A H 0.4780 0.7943 0.1459 0.033 Uiso 1 1 calc R . . H32B H 0.5869 0.7479 0.1138 0.033 Uiso 1 1 calc R . . C33 C -0.3607(2) 0.30880(16) 0.21355(6) 0.0329(4) Uani 1 1 d . . . H33A H -0.3268 0.2751 0.1887 0.040 Uiso 1 1 calc R . . H33B H -0.4087 0.3709 0.2055 0.040 Uiso 1 1 calc R . . C34 C -0.4624(2) 0.24397(16) 0.23576(6) 0.0316(4) Uani 1 1 d . . . H34 H -0.5021 0.2682 0.2603 0.038 Uiso 1 1 calc R . . C35 C -0.5005(2) 0.15609(19) 0.22373(7) 0.0468(6) Uani 1 1 d . . . H35A H -0.4627 0.1296 0.1993 0.056 Uiso 1 1 calc R . . H35B H -0.5659 0.1185 0.2394 0.056 Uiso 1 1 calc R . . C36 C -0.0484(3) 0.4131(2) -0.03319(7) 0.0555(7) Uani 1 1 d . . . H36A H -0.0574 0.3539 -0.0163 0.083 Uiso 0.70 1 calc PR A 1 H36B H -0.0837 0.3988 -0.0605 0.083 Uiso 0.70 1 calc PR A 1 H36C H -0.1046 0.4669 -0.0213 0.083 Uiso 0.70 1 calc PR A 1 H36D H -0.0679 0.4743 -0.0195 0.083 Uiso 0.30 1 d PR A 2 H36E H -0.0772 0.4182 -0.0610 0.083 Uiso 0.30 1 d PR A 2 H36F H -0.1004 0.3607 -0.0203 0.083 Uiso 0.30 1 d PR A 2 Si1 Si 0.13730(10) 0.44973(8) -0.03587(2) 0.03433(19) Uani 0.70 1 d P B 1 C37 C 0.1426(7) 0.5802(3) -0.05307(15) 0.0545(13) Uani 0.60 1 d P B 1 H37A H 0.0951 0.6222 -0.0330 0.082 Uiso 0.60 1 calc PR B 1 H37B H 0.0934 0.5860 -0.0792 0.082 Uiso 0.60 1 calc PR B 1 H37C H 0.2420 0.6012 -0.0561 0.082 Uiso 0.60 1 calc PR B 1 C38 C 0.2432(3) 0.3687(2) -0.07060(8) 0.0372(7) Uani 0.70 1 d PU B 1 C39 C 0.2273(5) 0.2614(3) -0.05675(16) 0.0572(12) Uani 0.70 1 d PU B 1 H39A H 0.1270 0.2418 -0.0586 0.086 Uiso 0.70 1 calc PR B 1 H39B H 0.2598 0.2553 -0.0286 0.086 Uiso 0.70 1 calc PR B 1 H39C H 0.2849 0.2185 -0.0742 0.086 Uiso 0.70 1 calc PR B 1 C40 C 0.1907(14) 0.3747(6) -0.1143(3) 0.061(2) Uani 0.60 1 d PU B 1 H40A H 0.2451 0.3285 -0.1311 0.092 Uiso 0.60 1 calc PR B 1 H40B H 0.2040 0.4421 -0.1245 0.092 Uiso 0.60 1 calc PR B 1 H40C H 0.0893 0.3575 -0.1153 0.092 Uiso 0.60 1 calc PR B 1 C41 C 0.4026(6) 0.3976(4) -0.06853(18) 0.0464(12) Uani 0.70 1 d PU B 1 H41A H 0.4368 0.3906 -0.0406 0.070 Uiso 0.70 1 calc PR B 1 H41B H 0.4140 0.4664 -0.0773 0.070 Uiso 0.70 1 calc PR B 1 H41C H 0.4579 0.3543 -0.0864 0.070 Uiso 0.70 1 calc PR B 1 Si1' Si 0.15530(19) 0.38408(15) -0.03044(5) 0.0220(3) Uani 0.30 1 d P B 2 C37' C 0.1808(10) 0.2499(5) -0.0358(3) 0.063(2) Uani 0.40 1 d P B 2 H37D H 0.2828 0.2345 -0.0348 0.094 Uiso 0.40 1 calc PR B 2 H37E H 0.1415 0.2280 -0.0618 0.094 Uiso 0.40 1 calc PR B 2 H37F H 0.1317 0.2157 -0.0137 0.094 Uiso 0.40 1 calc PR B 2 C38' C 0.2476(7) 0.4546(5) -0.07190(17) 0.0311(14) Uani 0.30 1 d PU B 2 C39' C 0.2074(10) 0.5679(7) -0.0688(3) 0.046(2) Uani 0.30 1 d PU B 2 H39D H 0.2344 0.5931 -0.0420 0.069 Uiso 0.30 1 calc PR B 2 H39E H 0.1044 0.5759 -0.0727 0.069 Uiso 0.30 1 calc PR B 2 H39F H 0.2584 0.6050 -0.0898 0.069 Uiso 0.30 1 calc PR B 2 C40' C 0.1975(19) 0.4161(9) -0.1145(5) 0.054(3) Uani 0.40 1 d PU B 2 H40D H 0.2380 0.4580 -0.1358 0.081 Uiso 0.40 1 calc PR B 2 H40E H 0.0932 0.4183 -0.1160 0.081 Uiso 0.40 1 calc PR B 2 H40F H 0.2300 0.3479 -0.1183 0.081 Uiso 0.40 1 calc PR B 2 C41' C 0.4109(12) 0.4465(9) -0.0665(3) 0.039(2) Uani 0.30 1 d PU B 2 H41D H 0.4401 0.3774 -0.0696 0.058 Uiso 0.30 1 calc PR B 2 H41E H 0.4374 0.4700 -0.0395 0.058 Uiso 0.30 1 calc PR B 2 H41F H 0.4586 0.4869 -0.0871 0.058 Uiso 0.30 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0310(3) 0.0489(3) 0.0470(3) -0.0047(2) -0.0018(2) -0.0155(2) O1 0.0441(9) 0.0475(9) 0.0207(6) -0.0063(6) 0.0119(6) -0.0103(7) O2 0.0191(6) 0.0244(6) 0.0216(6) 0.0048(5) 0.0020(5) -0.0021(5) O3 0.0273(7) 0.0416(8) 0.0482(9) 0.0122(7) -0.0097(7) -0.0018(6) O4 0.0167(6) 0.0298(6) 0.0225(6) 0.0055(5) 0.0024(5) -0.0035(5) O5 0.0300(7) 0.0545(9) 0.0249(7) 0.0006(6) 0.0092(5) -0.0140(7) C1 0.0348(11) 0.0386(11) 0.0247(10) -0.0050(8) 0.0095(8) -0.0144(9) C2 0.0453(13) 0.0496(13) 0.0242(10) -0.0088(9) 0.0079(9) -0.0192(11) C3 0.0354(11) 0.0404(11) 0.0181(9) -0.0033(8) 0.0092(8) -0.0076(9) C4 0.0297(10) 0.0295(10) 0.0186(9) -0.0005(7) 0.0068(7) -0.0036(8) C5 0.0230(9) 0.0231(8) 0.0193(8) 0.0019(7) 0.0055(7) -0.0004(8) C6 0.0194(9) 0.0223(8) 0.0223(8) 0.0061(7) 0.0043(7) -0.0024(7) C7 0.0179(9) 0.0248(9) 0.0205(8) 0.0004(7) 0.0021(7) -0.0019(7) C8 0.0183(8) 0.0210(8) 0.0192(8) 0.0037(7) 0.0030(6) 0.0006(7) C9 0.0197(8) 0.0230(9) 0.0191(8) 0.0024(7) 0.0033(7) 0.0005(7) C10 0.0276(10) 0.0238(9) 0.0224(9) -0.0003(7) 0.0076(7) -0.0025(8) C11 0.0246(9) 0.0263(9) 0.0217(9) 0.0014(7) 0.0040(7) -0.0028(8) C12 0.0210(9) 0.0242(9) 0.0222(8) 0.0060(7) 0.0030(7) 0.0015(7) C13 0.0164(8) 0.0226(8) 0.0199(8) 0.0051(7) 0.0050(6) 0.0029(7) C14 0.0210(9) 0.0195(8) 0.0200(8) 0.0041(7) 0.0044(7) 0.0033(7) C15 0.0281(10) 0.0252(9) 0.0236(9) 0.0001(7) 0.0052(7) 0.0001(8) C16 0.0361(11) 0.0216(9) 0.0262(9) 0.0010(7) 0.0106(8) 0.0013(8) C17 0.0236(9) 0.0260(9) 0.0234(9) 0.0028(7) 0.0071(7) 0.0065(8) C18 0.0219(9) 0.0315(10) 0.0227(9) 0.0040(7) 0.0054(7) 0.0060(8) C19 0.0355(11) 0.0241(9) 0.0310(10) 0.0010(8) 0.0141(8) 0.0002(8) C20 0.0237(9) 0.0323(10) 0.0222(9) 0.0007(7) 0.0089(7) -0.0024(8) C21 0.0339(11) 0.0434(11) 0.0289(10) 0.0008(9) 0.0148(8) 0.0049(9) C22 0.0321(10) 0.0244(9) 0.0216(9) 0.0012(7) 0.0051(7) -0.0026(8) C23 0.0459(12) 0.0307(10) 0.0203(9) 0.0023(8) 0.0070(8) -0.0067(9) C24 0.0474(13) 0.0296(10) 0.0292(10) 0.0068(8) -0.0045(9) -0.0137(9) C25 0.0543(15) 0.0526(14) 0.0412(13) 0.0169(11) -0.0147(11) -0.0250(12) C26 0.0583(18) 0.076(2) 0.081(2) 0.0480(17) -0.0272(15) -0.0225(15) C27 0.113(3) 0.119(3) 0.0248(13) 0.0062(15) -0.0161(15) -0.042(2) C28 0.0344(11) 0.0400(11) 0.0302(10) -0.0024(9) 0.0150(9) 0.0021(9) C29 0.0397(12) 0.0360(11) 0.0184(9) 0.0018(8) 0.0073(8) -0.0079(9) C30 0.0266(10) 0.0241(9) 0.0268(9) 0.0065(7) 0.0075(8) 0.0081(8) C31 0.0194(9) 0.0302(10) 0.0218(9) -0.0007(7) 0.0038(7) 0.0014(8) C32 0.0228(10) 0.0318(10) 0.0280(10) -0.0034(8) 0.0022(8) -0.0042(8) C33 0.0231(10) 0.0486(12) 0.0272(10) 0.0105(9) -0.0031(8) -0.0029(9) C34 0.0145(9) 0.0515(13) 0.0288(10) 0.0064(9) -0.0011(7) -0.0027(9) C35 0.0318(12) 0.0662(16) 0.0423(12) 0.0066(11) -0.0064(10) -0.0193(11) C36 0.0390(14) 0.0871(19) 0.0404(13) 0.0086(13) 0.0045(11) 0.0140(14) Si1 0.0421(5) 0.0387(5) 0.0223(4) -0.0013(4) 0.0032(3) 0.0056(4) C37 0.086(4) 0.035(2) 0.043(3) 0.009(2) -0.001(2) 0.009(3) C38 0.0426(18) 0.0437(18) 0.0253(14) -0.0085(13) 0.0018(12) -0.0011(14) C39 0.048(3) 0.047(2) 0.076(3) -0.010(2) 0.017(2) -0.0030(19) C40 0.074(5) 0.084(6) 0.026(3) -0.019(4) -0.009(3) 0.021(5) C41 0.042(2) 0.061(3) 0.036(2) -0.008(2) 0.0123(16) -0.008(3) Si1' 0.0243(9) 0.0203(9) 0.0213(8) 0.0020(7) 0.0006(6) -0.0021(7) C37' 0.070(6) 0.031(3) 0.086(6) -0.010(4) -0.021(5) -0.005(4) C38' 0.036(4) 0.044(4) 0.013(3) -0.001(3) -0.006(2) -0.007(3) C39' 0.042(5) 0.041(5) 0.054(6) 0.038(4) -0.003(4) -0.014(4) C40' 0.047(5) 0.098(9) 0.018(4) -0.010(6) 0.008(3) 0.002(7) C41' 0.029(4) 0.070(7) 0.017(4) -0.003(5) 0.012(3) -0.001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C32 1.7716(19) . ? O1 C3 1.435(2) . ? O1 Si1' 1.591(2) . ? O1 Si1 1.7032(16) . ? O2 C31 1.335(2) . ? O2 C6 1.466(2) . ? O3 C31 1.196(2) . ? O4 C33 1.432(2) . ? O4 C12 1.444(2) . ? O5 C20 1.437(2) . ? O5 H5 0.8400 . ? C1 C2 1.526(3) . ? C1 C10 1.541(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.509(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.558(3) . ? C3 H3 1.0000 . ? C4 C28 1.531(3) . ? C4 C29 1.540(3) . ? C4 C5 1.572(2) . ? C5 C6 1.533(2) . ? C5 C10 1.576(2) . ? C5 H5A 1.0000 . ? C6 C7 1.534(2) . ? C6 H6 1.0000 . ? C7 C8 1.541(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C18 1.540(2) . ? C8 C9 1.559(2) . ? C8 C14 1.580(2) . ? C9 C11 1.537(2) . ? C9 C10 1.572(2) . ? C9 H9 1.0000 . ? C10 C19 1.557(3) . ? C11 C12 1.537(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.522(2) . ? C12 H12 1.0000 . ? C13 C17 1.556(2) . ? C13 C14 1.560(2) . ? C13 H13 1.0000 . ? C14 C15 1.539(2) . ? C14 C30 1.552(2) . ? C15 C16 1.536(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.568(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C20 1.553(2) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C22 1.526(3) . ? C20 C21 1.534(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.535(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.498(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.326(3) . ? C24 H24 0.9500 . ? C25 C27 1.495(4) . ? C25 C26 1.511(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.511(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.489(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.304(3) . ? C34 H34 0.9500 . ? C35 H35A 0.9500 . ? C35 H35B 0.9500 . ? C36 Si1 1.814(3) . ? C36 Si1' 1.953(3) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C36 H36D 0.9600 . ? C36 H36E 0.9600 . ? C36 H36F 0.9600 . ? Si1 C37 1.855(5) . ? Si1 C38 1.872(3) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C40 1.525(12) . ? C38 C39 1.529(6) . ? C38 C41 1.547(6) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? Si1' C37' 1.840(8) . ? Si1' C38' 1.880(7) . ? C37' H37D 0.9800 . ? C37' H37E 0.9800 . ? C37' H37F 0.9800 . ? C38' C41' 1.546(14) . ? C38' C40' 1.572(16) . ? C38' C39' 1.583(12) . ? C39' H39D 0.9800 . ? C39' H39E 0.9800 . ? C39' H39F 0.9800 . ? C40' H40D 0.9800 . ? C40' H40E 0.9800 . ? C40' H40F 0.9800 . ? C41' H41D 0.9800 . ? C41' H41E 0.9800 . ? C41' H41F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 Si1' 131.55(14) . . ? C3 O1 Si1 126.74(14) . . ? Si1' O1 Si1 32.28(7) . . ? C31 O2 C6 117.40(13) . . ? C33 O4 C12 113.79(13) . . ? C20 O5 H5 109.5 . . ? C2 C1 C10 113.38(16) . . ? C2 C1 H1A 108.9 . . ? C10 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? C10 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 110.36(17) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O1 C3 C2 109.30(16) . . ? O1 C3 C4 109.07(15) . . ? C2 C3 C4 113.89(16) . . ? O1 C3 H3 108.1 . . ? C2 C3 H3 108.1 . . ? C4 C3 H3 108.1 . . ? C28 C4 C29 107.57(15) . . ? C28 C4 C3 111.43(15) . . ? C29 C4 C3 104.97(15) . . ? C28 C4 C5 114.48(15) . . ? C29 C4 C5 111.56(14) . . ? C3 C4 C5 106.45(14) . . ? C6 C5 C4 116.56(14) . . ? C6 C5 C10 107.25(13) . . ? C4 C5 C10 116.23(14) . . ? C6 C5 H5A 105.2 . . ? C4 C5 H5A 105.2 . . ? C10 C5 H5A 105.2 . . ? O2 C6 C5 109.74(13) . . ? O2 C6 C7 104.14(13) . . ? C5 C6 C7 111.25(14) . . ? O2 C6 H6 110.5 . . ? C5 C6 H6 110.5 . . ? C7 C6 H6 110.5 . . ? C6 C7 C8 113.63(14) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C18 C8 C7 107.58(14) . . ? C18 C8 C9 113.26(14) . . ? C7 C8 C9 107.33(13) . . ? C18 C8 C14 110.20(13) . . ? C7 C8 C14 110.74(14) . . ? C9 C8 C14 107.72(13) . . ? C11 C9 C8 111.49(14) . . ? C11 C9 C10 114.41(14) . . ? C8 C9 C10 115.84(14) . . ? C11 C9 H9 104.5 . . ? C8 C9 H9 104.5 . . ? C10 C9 H9 104.5 . . ? C1 C10 C19 107.23(16) . . ? C1 C10 C9 107.13(15) . . ? C19 C10 C9 112.89(14) . . ? C1 C10 C5 107.77(14) . . ? C19 C10 C5 114.52(15) . . ? C9 C10 C5 106.96(13) . . ? C9 C11 C12 112.10(15) . . ? C9 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? C9 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? O4 C12 C13 110.20(13) . . ? O4 C12 C11 108.91(14) . . ? C13 C12 C11 109.35(14) . . ? O4 C12 H12 109.5 . . ? C13 C12 H12 109.5 . . ? C11 C12 H12 109.5 . . ? C12 C13 C17 120.36(15) . . ? C12 C13 C14 109.45(13) . . ? C17 C13 C14 104.32(14) . . ? C12 C13 H13 107.4 . . ? C17 C13 H13 107.4 . . ? C14 C13 H13 107.4 . . ? C15 C14 C30 106.38(14) . . ? C15 C14 C13 100.20(13) . . ? C30 C14 C13 111.19(14) . . ? C15 C14 C8 116.54(14) . . ? C30 C14 C8 111.76(13) . . ? C13 C14 C8 110.18(13) . . ? C16 C15 C14 103.54(15) . . ? C16 C15 H15A 111.1 . . ? C14 C15 H15A 111.1 . . ? C16 C15 H15B 111.1 . . ? C14 C15 H15B 111.1 . . ? H15A C15 H15B 109.0 . . ? C15 C16 C17 107.03(14) . . ? C15 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? C15 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.6 . . ? C20 C17 C13 118.72(15) . . ? C20 C17 C16 112.24(14) . . ? C13 C17 C16 103.35(14) . . ? C20 C17 H17 107.3 . . ? C13 C17 H17 107.3 . . ? C16 C17 H17 107.3 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 C22 109.17(15) . . ? O5 C20 C21 104.14(15) . . ? C22 C20 C21 112.01(16) . . ? O5 C20 C17 109.87(14) . . ? C22 C20 C17 112.37(14) . . ? C21 C20 C17 108.96(15) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 C23 115.58(16) . . ? C20 C22 H22A 108.4 . . ? C23 C22 H22A 108.4 . . ? C20 C22 H22B 108.4 . . ? C23 C22 H22B 108.4 . . ? H22A C22 H22B 107.4 . . ? C24 C23 C22 111.93(17) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 128.9(2) . . ? C25 C24 H24 115.6 . . ? C23 C24 H24 115.6 . . ? C24 C25 C27 123.8(3) . . ? C24 C25 C26 121.0(3) . . ? C27 C25 C26 115.2(2) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C4 C28 H28A 109.5 . . ? C4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C4 C29 H29A 109.5 . . ? C4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C14 C30 H30A 109.5 . . ? C14 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C14 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O3 C31 O2 125.71(17) . . ? O3 C31 C32 127.01(17) . . ? O2 C31 C32 107.28(15) . . ? C31 C32 Cl1 112.10(13) . . ? C31 C32 H32A 109.2 . . ? Cl1 C32 H32A 109.2 . . ? C31 C32 H32B 109.2 . . ? Cl1 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? O4 C33 C34 108.58(14) . . ? O4 C33 H33A 110.0 . . ? C34 C33 H33A 110.0 . . ? O4 C33 H33B 110.0 . . ? C34 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? C35 C34 C33 124.3(2) . . ? C35 C34 H34 117.9 . . ? C33 C34 H34 117.9 . . ? C34 C35 H35A 120.0 . . ? C34 C35 H35B 120.0 . . ? H35A C35 H35B 120.0 . . ? Si1 C36 Si1' 28.02(7) . . ? Si1 C36 H36A 109.5 . . ? Si1' C36 H36A 83.8 . . ? Si1 C36 H36B 109.5 . . ? Si1' C36 H36B 109.4 . . ? H36A C36 H36B 109.5 . . ? Si1 C36 H36C 109.5 . . ? Si1' C36 H36C 131.1 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? Si1 C36 H36D 88.3 . . ? Si1' C36 H36D 109.8 . . ? H36A C36 H36D 114.9 . . ? H36B C36 H36D 122.6 . . ? H36C C36 H36D 21.5 . . ? Si1 C36 H36E 101.8 . . ? Si1' C36 H36E 109.5 . . ? H36A C36 H36E 125.4 . . ? H36B C36 H36E 16.0 . . ? H36C C36 H36E 100.2 . . ? H36D C36 H36E 109.5 . . ? Si1 C36 H36F 135.4 . . ? Si1' C36 H36F 109.1 . . ? H36A C36 H36F 25.9 . . ? H36B C36 H36F 95.1 . . ? H36C C36 H36F 95.7 . . ? H36D C36 H36F 109.5 . . ? H36E C36 H36F 109.5 . . ? O1 Si1 C36 112.12(10) . . ? O1 Si1 C37 112.59(19) . . ? C36 Si1 C37 107.5(2) . . ? O1 Si1 C38 101.48(12) . . ? C36 Si1 C38 112.31(14) . . ? C37 Si1 C38 110.9(2) . . ? C40 C38 C39 107.6(4) . . ? C40 C38 C41 109.9(6) . . ? C39 C38 C41 108.8(3) . . ? C40 C38 Si1 112.0(4) . . ? C39 C38 Si1 108.8(2) . . ? C41 C38 Si1 109.7(2) . . ? O1 Si1' C37' 115.6(3) . . ? O1 Si1' C38' 101.6(2) . . ? C37' Si1' C38' 111.8(4) . . ? O1 Si1' C36 110.44(14) . . ? C37' Si1' C36 108.7(3) . . ? C38' Si1' C36 108.3(2) . . ? Si1' C37' H37D 109.5 . . ? Si1' C37' H37E 109.5 . . ? H37D C37' H37E 109.5 . . ? Si1' C37' H37F 109.5 . . ? H37D C37' H37F 109.5 . . ? H37E C37' H37F 109.5 . . ? C41' C38' C40' 112.1(8) . . ? C41' C38' C39' 107.3(7) . . ? C40' C38' C39' 108.0(7) . . ? C41' C38' Si1' 109.7(5) . . ? C40' C38' Si1' 110.2(7) . . ? C39' C38' Si1' 109.6(5) . . ? C38' C39' H39D 109.5 . . ? C38' C39' H39E 109.5 . . ? H39D C39' H39E 109.5 . . ? C38' C39' H39F 109.5 . . ? H39D C39' H39F 109.5 . . ? H39E C39' H39F 109.5 . . ? C38' C40' H40D 109.5 . . ? C38' C40' H40E 109.5 . . ? H40D C40' H40E 109.5 . . ? C38' C40' H40F 109.5 . . ? H40D C40' H40F 109.5 . . ? H40E C40' H40F 109.5 . . ? C38' C41' H41D 109.5 . . ? C38' C41' H41E 109.5 . . ? H41D C41' H41E 109.5 . . ? C38' C41' H41F 109.5 . . ? H41D C41' H41F 109.5 . . ? H41E C41' H41F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -58.4(2) . . . . ? Si1' O1 C3 C2 48.2(3) . . . . ? Si1 O1 C3 C2 89.8(2) . . . . ? Si1' O1 C3 C4 173.29(17) . . . . ? Si1 O1 C3 C4 -145.14(14) . . . . ? C1 C2 C3 O1 -178.41(18) . . . . ? C1 C2 C3 C4 59.3(2) . . . . ? O1 C3 C4 C28 -51.7(2) . . . . ? C2 C3 C4 C28 70.7(2) . . . . ? O1 C3 C4 C29 64.45(19) . . . . ? C2 C3 C4 C29 -173.16(16) . . . . ? O1 C3 C4 C5 -177.15(15) . . . . ? C2 C3 C4 C5 -54.8(2) . . . . ? C28 C4 C5 C6 56.7(2) . . . . ? C29 C4 C5 C6 -65.7(2) . . . . ? C3 C4 C5 C6 -179.69(15) . . . . ? C28 C4 C5 C10 -71.3(2) . . . . ? C29 C4 C5 C10 166.28(16) . . . . ? C3 C4 C5 C10 52.3(2) . . . . ? C31 O2 C6 C5 -153.43(14) . . . . ? C31 O2 C6 C7 87.39(16) . . . . ? C4 C5 C6 O2 49.78(19) . . . . ? C10 C5 C6 O2 -177.96(13) . . . . ? C4 C5 C6 C7 164.49(14) . . . . ? C10 C5 C6 C7 -63.25(18) . . . . ? O2 C6 C7 C8 178.33(13) . . . . ? C5 C6 C7 C8 60.19(19) . . . . ? C6 C7 C8 C18 71.25(18) . . . . ? C6 C7 C8 C9 -50.94(18) . . . . ? C6 C7 C8 C14 -168.26(14) . . . . ? C18 C8 C9 C11 66.58(18) . . . . ? C7 C8 C9 C11 -174.83(14) . . . . ? C14 C8 C9 C11 -55.55(18) . . . . ? C18 C8 C9 C10 -66.59(18) . . . . ? C7 C8 C9 C10 52.00(18) . . . . ? C14 C8 C9 C10 171.28(13) . . . . ? C2 C1 C10 C19 -70.4(2) . . . . ? C2 C1 C10 C9 168.19(17) . . . . ? C2 C1 C10 C5 53.4(2) . . . . ? C11 C9 C10 C1 54.74(19) . . . . ? C8 C9 C10 C1 -173.44(15) . . . . ? C11 C9 C10 C19 -63.1(2) . . . . ? C8 C9 C10 C19 68.75(19) . . . . ? C11 C9 C10 C5 170.08(14) . . . . ? C8 C9 C10 C5 -58.10(18) . . . . ? C6 C5 C10 C1 175.16(15) . . . . ? C4 C5 C10 C1 -52.4(2) . . . . ? C6 C5 C10 C19 -65.63(18) . . . . ? C4 C5 C10 C19 66.8(2) . . . . ? C6 C5 C10 C9 60.25(17) . . . . ? C4 C5 C10 C9 -167.31(15) . . . . ? C8 C9 C11 C12 56.71(19) . . . . ? C10 C9 C11 C12 -169.42(14) . . . . ? C33 O4 C12 C13 159.79(15) . . . . ? C33 O4 C12 C11 -80.25(17) . . . . ? C9 C11 C12 O4 -178.57(14) . . . . ? C9 C11 C12 C13 -58.09(18) . . . . ? O4 C12 C13 C17 -59.4(2) . . . . ? C11 C12 C13 C17 -179.12(15) . . . . ? O4 C12 C13 C14 179.85(13) . . . . ? C11 C12 C13 C14 60.17(17) . . . . ? C12 C13 C14 C15 174.61(14) . . . . ? C17 C13 C14 C15 44.57(16) . . . . ? C12 C13 C14 C30 62.46(17) . . . . ? C17 C13 C14 C30 -67.58(17) . . . . ? C12 C13 C14 C8 -62.03(17) . . . . ? C17 C13 C14 C8 167.93(14) . . . . ? C18 C8 C14 C15 47.6(2) . . . . ? C7 C8 C14 C15 -71.29(18) . . . . ? C9 C8 C14 C15 171.63(14) . . . . ? C18 C8 C14 C30 170.23(15) . . . . ? C7 C8 C14 C30 51.32(19) . . . . ? C9 C8 C14 C30 -65.76(17) . . . . ? C18 C8 C14 C13 -65.61(18) . . . . ? C7 C8 C14 C13 175.48(13) . . . . ? C9 C8 C14 C13 58.40(17) . . . . ? C30 C14 C15 C16 72.08(16) . . . . ? C13 C14 C15 C16 -43.75(16) . . . . ? C8 C14 C15 C16 -162.55(14) . . . . ? C14 C15 C16 C17 27.43(18) . . . . ? C12 C13 C17 C20 84.1(2) . . . . ? C14 C13 C17 C20 -152.72(16) . . . . ? C12 C13 C17 C16 -150.94(15) . . . . ? C14 C13 C17 C16 -27.73(16) . . . . ? C15 C16 C17 C20 129.45(15) . . . . ? C15 C16 C17 C13 0.36(18) . . . . ? C13 C17 C20 O5 -67.9(2) . . . . ? C16 C17 C20 O5 171.53(14) . . . . ? C13 C17 C20 C22 53.8(2) . . . . ? C16 C17 C20 C22 -66.71(19) . . . . ? C13 C17 C20 C21 178.59(16) . . . . ? C16 C17 C20 C21 58.0(2) . . . . ? O5 C20 C22 C23 -62.6(2) . . . . ? C21 C20 C22 C23 52.2(2) . . . . ? C17 C20 C22 C23 175.21(16) . . . . ? C20 C22 C23 C24 172.37(16) . . . . ? C22 C23 C24 C25 134.7(2) . . . . ? C23 C24 C25 C27 1.0(4) . . . . ? C23 C24 C25 C26 -179.3(2) . . . . ? C6 O2 C31 O3 9.6(3) . . . . ? C6 O2 C31 C32 -170.64(13) . . . . ? O3 C31 C32 Cl1 -13.3(2) . . . . ? O2 C31 C32 Cl1 166.94(12) . . . . ? C12 O4 C33 C34 -168.75(16) . . . . ? O4 C33 C34 C35 -120.7(2) . . . . ? C3 O1 Si1 C36 -38.1(2) . . . . ? Si1' O1 Si1 C36 73.45(17) . . . . ? C3 O1 Si1 C37 83.2(3) . . . . ? Si1' O1 Si1 C37 -165.2(3) . . . . ? C3 O1 Si1 C38 -158.19(18) . . . . ? Si1' O1 Si1 C38 -46.60(16) . . . . ? Si1' C36 Si1 O1 -62.55(13) . . . . ? Si1' C36 Si1 C37 173.2(2) . . . . ? Si1' C36 Si1 C38 50.97(15) . . . . ? O1 Si1 C38 C40 -177.3(5) . . . . ? C36 Si1 C38 C40 62.8(5) . . . . ? C37 Si1 C38 C40 -57.5(5) . . . . ? O1 Si1 C38 C39 63.9(3) . . . . ? C36 Si1 C38 C39 -56.0(3) . . . . ? C37 Si1 C38 C39 -176.3(3) . . . . ? O1 Si1 C38 C41 -55.0(3) . . . . ? C36 Si1 C38 C41 -174.9(3) . . . . ? C37 Si1 C38 C41 64.9(4) . . . . ? C3 O1 Si1' C37' -90.2(4) . . . . ? Si1 O1 Si1' C37' 174.4(4) . . . . ? C3 O1 Si1' C38' 148.5(3) . . . . ? Si1 O1 Si1' C38' 53.2(2) . . . . ? C3 O1 Si1' C36 33.7(3) . . . . ? Si1 O1 Si1' C36 -61.63(16) . . . . ? Si1 C36 Si1' O1 69.94(14) . . . . ? Si1 C36 Si1' C37' -162.2(4) . . . . ? Si1 C36 Si1' C38' -40.5(2) . . . . ? O1 Si1' C38' C41' 54.8(6) . . . . ? C37' Si1' C38' C41' -69.0(7) . . . . ? C36 Si1' C38' C41' 171.2(5) . . . . ? O1 Si1' C38' C40' 178.6(7) . . . . ? C37' Si1' C38' C40' 54.8(8) . . . . ? C36 Si1' C38' C40' -65.0(8) . . . . ? O1 Si1' C38' C39' -62.8(5) . . . . ? C37' Si1' C38' C39' 173.4(5) . . . . ? C36 Si1' C38' C39' 53.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O4 0.84 1.87 2.6968(17) 165.7 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.212 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 876477' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu_dm11511_0m #TrackingRef '3,12-Di-O-acetyl-protopanaxadiol.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C69 H114 Cl2 O10' _chemical_formula_weight 1174.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.2356(2) _cell_length_b 11.9742(3) _cell_length_c 24.8296(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.4470(10) _cell_angle_gamma 90.00 _cell_volume 3334.46(13) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 9933 _cell_measurement_theta_min 3.57 _cell_measurement_theta_max 65.76 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 1.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7358 _exptl_absorpt_correction_T_max 0.7987 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29181 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 66.33 _reflns_number_total 10458 _reflns_number_gt 10113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+1.9065P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.071(19) _chemical_absolute_configuration ad _refine_ls_number_reflns 10458 _refine_ls_number_parameters 779 _refine_ls_number_restraints 41 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2625(2) -0.14305(19) 0.17300(9) 0.0372(5) Uani 1 1 d . . . O2 O 0.1746(3) -0.1244(2) 0.25181(10) 0.0541(7) Uani 1 1 d . . . O3 O 0.80305(16) 0.39979(16) 0.14084(8) 0.0256(4) Uani 1 1 d . . . O4 O 0.87128(19) 0.3747(3) 0.22662(9) 0.0460(6) Uani 1 1 d . . . O5 O 0.84688(19) 0.62930(19) 0.16603(8) 0.0325(5) Uani 1 1 d . . . H5 H 0.8448 0.6728 0.1925 0.049 Uiso 1 1 calc R . . O1' O 0.21670(19) 1.26150(17) 0.33737(8) 0.0318(5) Uani 1 1 d . . . O2' O 0.2039(3) 1.2697(3) 0.24712(11) 0.0678(9) Uani 1 1 d . . . O3' O 0.76453(18) 0.71006(17) 0.34864(8) 0.0284(4) Uani 1 1 d . . . O4' O 0.7940(3) 0.7399(2) 0.26130(10) 0.0471(6) Uani 1 1 d . . . O5' O 0.7708(3) 0.49230(19) 0.31086(10) 0.0510(7) Uani 1 1 d . . . H5' H 0.7822 0.4450 0.2867 0.077 Uiso 1 1 calc R . . C1 C 0.5000(3) 0.0777(3) 0.17327(13) 0.0320(7) Uani 1 1 d . . . H1A H 0.5873 0.0692 0.1713 0.038 Uiso 1 1 calc R . . H1B H 0.4857 0.1163 0.2075 0.038 Uiso 1 1 calc R . . C2 C 0.4435(3) -0.0379(3) 0.17410(14) 0.0329(7) Uani 1 1 d . . . H2A H 0.4748 -0.0790 0.2066 0.040 Uiso 1 1 calc R . . H2B H 0.4650 -0.0805 0.1419 0.040 Uiso 1 1 calc R . . C3 C 0.3082(3) -0.0289(3) 0.17454(12) 0.0311(7) Uani 1 1 d . . . H3 H 0.2870 0.0072 0.2090 0.037 Uiso 1 1 calc R . . C4 C 0.2498(3) 0.0366(3) 0.12685(13) 0.0327(7) Uani 1 1 d . . . C5 C 0.3128(3) 0.1522(3) 0.12680(12) 0.0270(6) Uani 1 1 d . . . H5A H 0.2966 0.1861 0.1624 0.032 Uiso 1 1 calc R . . C6 C 0.2579(3) 0.2343(3) 0.08495(13) 0.0336(7) Uani 1 1 d . . . H6A H 0.2806 0.2121 0.0485 0.040 Uiso 1 1 calc R . . H6B H 0.1699 0.2313 0.0853 0.040 Uiso 1 1 calc R . . C7 C 0.3003(3) 0.3533(3) 0.09677(13) 0.0324(7) Uani 1 1 d . . . H7A H 0.2709 0.3774 0.1317 0.039 Uiso 1 1 calc R . . H7B H 0.2649 0.4036 0.0685 0.039 Uiso 1 1 calc R . . C8 C 0.4369(2) 0.3654(2) 0.09901(11) 0.0256(6) Uani 1 1 d . . . C9 C 0.4939(3) 0.2743(2) 0.13676(11) 0.0253(6) Uani 1 1 d . . . H9 H 0.4669 0.2925 0.1734 0.030 Uiso 1 1 calc R . . C10 C 0.4518(2) 0.1512(3) 0.12574(12) 0.0274(6) Uani 1 1 d . . . C11 C 0.6296(3) 0.2857(2) 0.14197(13) 0.0291(6) Uani 1 1 d . . . H11C H 0.6608 0.2344 0.1707 0.035 Uiso 1 1 calc R . . H11D H 0.6617 0.2607 0.1077 0.035 Uiso 1 1 calc R . . C12 C 0.6778(2) 0.4026(2) 0.15480(11) 0.0252(6) Uani 1 1 d . . . H12 H 0.6728 0.4193 0.1941 0.030 Uiso 1 1 calc R . . C13 C 0.6158(2) 0.4929(2) 0.12106(11) 0.0247(6) Uani 1 1 d . . . H13 H 0.6355 0.4796 0.0828 0.030 Uiso 1 1 calc R . . C14 C 0.4778(2) 0.4812(3) 0.12298(11) 0.0254(6) Uani 1 1 d . . . C15 C 0.4343(3) 0.5852(3) 0.09110(13) 0.0329(7) Uani 1 1 d . . . H15C H 0.3590 0.6134 0.1048 0.039 Uiso 1 1 calc R . . H15D H 0.4205 0.5672 0.0523 0.039 Uiso 1 1 calc R . . C16 C 0.5341(3) 0.6728(3) 0.09957(15) 0.0380(7) Uani 1 1 d . . . H16C H 0.5046 0.7384 0.1190 0.046 Uiso 1 1 calc R . . H16D H 0.5608 0.6981 0.0643 0.046 Uiso 1 1 calc R . . C17 C 0.6386(3) 0.6178(3) 0.13291(11) 0.0282(6) Uani 1 1 d . . . H17 H 0.6239 0.6300 0.1718 0.034 Uiso 1 1 calc R . . C18 C 0.4759(3) 0.3546(3) 0.04001(12) 0.0341(7) Uani 1 1 d . . . H18D H 0.4255 0.2993 0.0205 0.051 Uiso 1 1 calc R . . H18E H 0.5594 0.3305 0.0406 0.051 Uiso 1 1 calc R . . H18F H 0.4675 0.4270 0.0219 0.051 Uiso 1 1 calc R . . C19 C 0.4987(3) 0.1022(3) 0.07329(13) 0.0357(7) Uani 1 1 d . . . H19D H 0.5778 0.1329 0.0677 0.054 Uiso 1 1 calc R . . H19E H 0.4438 0.1220 0.0426 0.054 Uiso 1 1 calc R . . H19F H 0.5040 0.0208 0.0764 0.054 Uiso 1 1 calc R . . C20 C 0.7636(3) 0.6667(3) 0.12361(12) 0.0310(7) Uani 1 1 d . . . C21 C 0.7584(3) 0.7953(3) 0.12562(15) 0.0387(8) Uani 1 1 d . . . H21D H 0.7210 0.8188 0.1584 0.058 Uiso 1 1 calc R . . H21E H 0.7114 0.8231 0.0939 0.058 Uiso 1 1 calc R . . H21F H 0.8394 0.8256 0.1258 0.058 Uiso 1 1 calc R . . C22 C 0.8142(3) 0.6262(3) 0.07112(12) 0.0310(7) Uani 1 1 d . . . H22C H 0.8194 0.5437 0.0721 0.037 Uiso 1 1 calc R . . H22D H 0.7575 0.6467 0.0406 0.037 Uiso 1 1 calc R . . C23 C 0.9366(3) 0.6731(3) 0.06022(15) 0.0417(8) Uani 1 1 d . . . H23C H 0.9264 0.7460 0.0418 0.050 Uiso 1 1 calc R . . H23D H 0.9820 0.6861 0.0951 0.050 Uiso 1 1 calc R . . C24 C 1.0074(3) 0.5971(3) 0.02620(14) 0.0384(7) Uani 1 1 d . . . H24 H 0.9904 0.5197 0.0295 0.046 Uiso 1 1 calc R . . C25 C 1.0901(3) 0.6221(3) -0.00778(12) 0.0318(7) Uani 1 1 d . . . C26 C 1.1562(3) 0.5337(3) -0.03657(15) 0.0431(8) Uani 1 1 d . . . H26A H 1.1250 0.4600 -0.0276 0.065 Uiso 1 1 calc R . . H26B H 1.2412 0.5375 -0.0254 0.065 Uiso 1 1 calc R . . H26C H 1.1455 0.5457 -0.0756 0.065 Uiso 1 1 calc R . . C27 C 1.1282(5) 0.7393(4) -0.01960(19) 0.0637(12) Uani 1 1 d . . . H27A H 1.0697 0.7921 -0.0066 0.096 Uiso 1 1 calc R . . H27B H 1.1334 0.7486 -0.0586 0.096 Uiso 1 1 calc R . . H27C H 1.2064 0.7539 -0.0013 0.096 Uiso 1 1 calc R . . C28 C 0.2517(4) -0.0295(3) 0.07405(14) 0.0444(8) Uani 1 1 d . . . H28D H 0.3329 -0.0558 0.0691 0.067 Uiso 1 1 calc R . . H28E H 0.2254 0.0187 0.0437 0.067 Uiso 1 1 calc R . . H28F H 0.1980 -0.0938 0.0755 0.067 Uiso 1 1 calc R . . C29 C 0.1181(3) 0.0538(3) 0.13899(15) 0.0407(8) Uani 1 1 d . . . H29D H 0.0809 -0.0188 0.1449 0.061 Uiso 1 1 calc R . . H29E H 0.0760 0.0913 0.1084 0.061 Uiso 1 1 calc R . . H29F H 0.1136 0.0999 0.1714 0.061 Uiso 1 1 calc R . . C30 C 0.4408(3) 0.4981(3) 0.18197(12) 0.0299(6) Uani 1 1 d . . . H30D H 0.4532 0.5763 0.1925 0.045 Uiso 1 1 calc R . . H30E H 0.4895 0.4498 0.2064 0.045 Uiso 1 1 calc R . . H30F H 0.3564 0.4788 0.1841 0.045 Uiso 1 1 calc R . . C31 C 0.1971(3) -0.1790(3) 0.21293(13) 0.0350(7) Uani 1 1 d . . . C32 C 0.1546(3) -0.2965(3) 0.20212(15) 0.0415(8) Uani 1 1 d . . . H32D H 0.1749 -0.3432 0.2338 0.062 Uiso 1 1 calc R . . H32E H 0.1932 -0.3266 0.1709 0.062 Uiso 1 1 calc R . . H32F H 0.0679 -0.2964 0.1947 0.062 Uiso 1 1 calc R . . C33 C 0.8885(3) 0.3895(3) 0.17998(12) 0.0308(6) Uani 1 1 d . . . C34 C 1.0101(3) 0.3979(3) 0.15762(13) 0.0374(7) Uani 1 1 d . . . H34D H 1.0358 0.4761 0.1581 0.056 Uiso 1 1 calc R . . H34E H 1.0062 0.3700 0.1205 0.056 Uiso 1 1 calc R . . H34F H 1.0672 0.3532 0.1798 0.056 Uiso 1 1 calc R . . C1' C 0.4544(3) 1.0403(2) 0.32676(12) 0.0283(6) Uani 1 1 d . . . H1'1 H 0.5411 1.0480 0.3228 0.034 Uiso 1 1 calc R . . H1'2 H 0.4200 0.9992 0.2949 0.034 Uiso 1 1 calc R . . C2' C 0.3983(3) 1.1567(3) 0.32789(13) 0.0308(6) Uani 1 1 d . . . H2'1 H 0.4372 1.2008 0.3577 0.037 Uiso 1 1 calc R . . H2'2 H 0.4111 1.1959 0.2936 0.037 Uiso 1 1 calc R . . C3' C 0.2662(3) 1.1484(2) 0.33554(13) 0.0298(6) Uani 1 1 d . . . H3' H 0.2269 1.1075 0.3042 0.036 Uiso 1 1 calc R . . C4' C 0.2362(3) 1.0897(3) 0.38771(12) 0.0306(6) Uani 1 1 d . . . C5' C 0.2981(3) 0.9732(3) 0.38656(12) 0.0278(6) Uani 1 1 d . . . H5'1 H 0.2609 0.9359 0.3537 0.033 Uiso 1 1 calc R . . C6' C 0.2685(3) 0.8964(3) 0.43309(14) 0.0365(7) Uani 1 1 d . . . H6'1 H 0.1827 0.9028 0.4396 0.044 Uiso 1 1 calc R . . H6'2 H 0.3149 0.9195 0.4664 0.044 Uiso 1 1 calc R . . C7' C 0.2981(3) 0.7749(3) 0.41984(14) 0.0350(7) Uani 1 1 d . . . H7'1 H 0.2463 0.7505 0.3884 0.042 Uiso 1 1 calc R . . H7'2 H 0.2801 0.7271 0.4509 0.042 Uiso 1 1 calc R . . C8' C 0.4294(3) 0.7579(2) 0.40719(12) 0.0263(6) Uani 1 1 d . . . C9' C 0.4672(2) 0.8477(2) 0.36588(11) 0.0242(6) Uani 1 1 d . . . H9' H 0.4211 0.8290 0.3314 0.029 Uiso 1 1 calc R . . C10' C 0.4343(2) 0.9720(2) 0.37793(11) 0.0243(6) Uani 1 1 d . . . C11' C 0.5981(3) 0.8325(2) 0.35389(12) 0.0280(6) Uani 1 1 d . . . H11A H 0.6480 0.8562 0.3861 0.034 Uiso 1 1 calc R . . H11B H 0.6160 0.8833 0.3240 0.034 Uiso 1 1 calc R . . C12' C 0.6353(3) 0.7129(2) 0.33863(12) 0.0282(6) Uani 1 1 d . . . H12' H 0.6134 0.6982 0.2996 0.034 Uiso 1 1 calc R . . C13' C 0.5841(3) 0.6227(2) 0.37332(12) 0.0270(6) Uani 1 1 d . . . H13' H 0.6255 0.6271 0.4101 0.032 Uiso 1 1 calc R . . C14' C 0.4486(3) 0.6421(2) 0.37931(12) 0.0281(6) Uani 1 1 d . . . C15' C 0.4166(3) 0.5373(3) 0.41187(14) 0.0356(7) Uani 1 1 d . . . H15A H 0.3313 0.5179 0.4052 0.043 Uiso 1 1 calc R . . H15B H 0.4335 0.5494 0.4510 0.043 Uiso 1 1 calc R . . C16' C 0.4975(3) 0.4446(3) 0.39065(16) 0.0408(8) Uani 1 1 d . . . H16A H 0.4488 0.3891 0.3696 0.049 Uiso 1 1 calc R . . H16B H 0.5402 0.4058 0.4213 0.049 Uiso 1 1 calc R . . C17' C 0.5885(3) 0.5003(2) 0.35422(13) 0.0341(7) Uani 1 1 d . . . H17' H 0.5522 0.4984 0.3165 0.041 Uiso 1 1 calc R . . C18' C 0.5033(3) 0.7657(3) 0.46151(12) 0.0333(7) Uani 1 1 d . . . H18A H 0.4760 0.8298 0.4820 0.050 Uiso 1 1 calc R . . H18B H 0.5877 0.7754 0.4548 0.050 Uiso 1 1 calc R . . H18C H 0.4931 0.6971 0.4822 0.050 Uiso 1 1 calc R . . C19' C 0.5119(3) 1.0222(3) 0.42515(13) 0.0336(7) Uani 1 1 d . . . H19A H 0.5924 0.9906 0.4254 0.050 Uiso 1 1 calc R . . H19B H 0.4765 1.0046 0.4593 0.050 Uiso 1 1 calc R . . H19C H 0.5162 1.1035 0.4208 0.050 Uiso 1 1 calc R . . C20' C 0.7100(3) 0.4402(3) 0.35358(13) 0.0353(7) Uani 1 1 d . . . C21' C 0.6866(4) 0.3171(3) 0.33845(17) 0.0481(9) Uani 1 1 d . . . H21A H 0.6266 0.3131 0.3082 0.072 Uiso 1 1 calc R . . H21B H 0.6574 0.2773 0.3695 0.072 Uiso 1 1 calc R . . H21C H 0.7608 0.2825 0.3280 0.072 Uiso 1 1 calc R . . C22' C 0.7872(3) 0.4538(3) 0.40523(14) 0.0377(7) Uani 1 1 d . . . H22A H 0.7399 0.4327 0.4360 0.045 Uiso 1 1 calc R . . H22B H 0.8089 0.5335 0.4095 0.045 Uiso 1 1 calc R . . C23' C 0.9017(3) 0.3841(3) 0.40764(17) 0.0497(9) Uani 1 1 d . . . H23A H 0.8817 0.3058 0.4161 0.060 Uiso 1 1 calc R . . H23B H 0.9351 0.3849 0.3716 0.060 Uiso 1 1 calc R . . C24' C 0.9942(3) 0.4246(4) 0.44826(17) 0.0532(10) Uani 1 1 d . . . H24' H 1.0245 0.4972 0.4419 0.064 Uiso 1 1 calc R . . C25' C 1.0406(4) 0.3735(5) 0.4924(2) 0.0801(13) Uani 1 1 d U . . C26' C 1.1372(5) 0.4238(6) 0.5279(2) 0.0954(16) Uani 1 1 d U . . H26D H 1.2109 0.3812 0.5248 0.143 Uiso 1 1 calc R . . H26E H 1.1145 0.4221 0.5654 0.143 Uiso 1 1 calc R . . H26F H 1.1498 0.5014 0.5170 0.143 Uiso 1 1 calc R . . C27' C 1.0014(5) 0.2565(6) 0.5097(2) 0.0870(15) Uani 1 1 d U . . H27D H 0.9378 0.2292 0.4843 0.131 Uiso 1 1 calc R . . H27E H 0.9718 0.2603 0.5460 0.131 Uiso 1 1 calc R . . H27F H 1.0695 0.2054 0.5099 0.131 Uiso 1 1 calc R . . C28' C 0.2703(3) 1.1608(3) 0.43776(13) 0.0354(7) Uani 1 1 d . . . H28A H 0.3539 1.1838 0.4370 0.053 Uiso 1 1 calc R . . H28B H 0.2594 1.1169 0.4704 0.053 Uiso 1 1 calc R . . H28C H 0.2193 1.2272 0.4378 0.053 Uiso 1 1 calc R . . C29' C 0.0999(3) 1.0726(3) 0.38532(16) 0.0416(8) Uani 1 1 d . . . H29A H 0.0771 1.0381 0.4190 0.062 Uiso 1 1 calc R . . H29B H 0.0761 1.0239 0.3549 0.062 Uiso 1 1 calc R . . H29C H 0.0601 1.1451 0.3806 0.062 Uiso 1 1 calc R . . C30' C 0.3780(3) 0.6339(3) 0.32384(14) 0.0372(7) Uani 1 1 d . . . H30A H 0.4211 0.6740 0.2966 0.056 Uiso 1 1 calc R . . H30B H 0.2989 0.6674 0.3264 0.056 Uiso 1 1 calc R . . H30C H 0.3693 0.5553 0.3134 0.056 Uiso 1 1 calc R . . C31' C 0.1886(3) 1.3113(3) 0.29009(14) 0.0367(7) Uani 1 1 d . . . C32' C 0.1356(3) 1.4241(3) 0.29753(15) 0.0379(7) Uani 1 1 d . . . H32A H 0.1738 1.4782 0.2744 0.057 Uiso 1 1 calc R . . H32B H 0.1484 1.4468 0.3354 0.057 Uiso 1 1 calc R . . H32C H 0.0499 1.4215 0.2877 0.057 Uiso 1 1 calc R . . C33' C 0.8330(3) 0.7205(3) 0.30705(14) 0.0380(8) Uani 1 1 d . . . C34' C 0.9627(3) 0.7069(4) 0.32392(18) 0.0551(11) Uani 1 1 d . . . H34A H 0.9887 0.6315 0.3147 0.083 Uiso 1 1 calc R . . H34B H 0.9745 0.7183 0.3630 0.083 Uiso 1 1 calc R . . H34C H 1.0095 0.7620 0.3051 0.083 Uiso 1 1 calc R . . C1S C 0.9137(6) 0.0723(9) 0.2579(3) 0.072(2) Uani 0.70 1 d PDU A 1 H1SA H 0.9396 0.1502 0.2649 0.086 Uiso 0.70 1 calc PR A 1 H1SB H 0.9860 0.0248 0.2593 0.086 Uiso 0.70 1 calc PR A 1 Cl1 Cl 0.8221(4) 0.0296(4) 0.30948(18) 0.0593(11) Uani 0.70 1 d PDU A 1 Cl2 Cl 0.84525(14) 0.06474(19) 0.19428(7) 0.0639(5) Uani 0.70 1 d PDU A 1 C1'S C 0.8972(11) -0.0019(11) 0.2522(4) 0.039(2) Uani 0.30 1 d PDU B 2 H1'A H 0.9831 -0.0192 0.2580 0.047 Uiso 0.30 1 calc PR B 2 H1'B H 0.8570 -0.0624 0.2309 0.047 Uiso 0.30 1 calc PR B 2 Cl1' Cl 0.8285(10) 0.0215(14) 0.3151(5) 0.087(4) Uani 0.30 1 d PDU B 2 Cl2' Cl 0.8739(8) 0.1266(8) 0.2222(5) 0.158(4) Uani 0.30 1 d PU B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0421(12) 0.0334(11) 0.0373(12) -0.0032(9) 0.0130(10) -0.0116(10) O2 0.0717(18) 0.0546(15) 0.0378(14) -0.0021(12) 0.0174(13) -0.0218(14) O3 0.0183(9) 0.0307(10) 0.0280(10) -0.0011(8) 0.0041(8) 0.0018(8) O4 0.0283(11) 0.0815(19) 0.0286(12) 0.0023(12) 0.0036(9) 0.0118(12) O5 0.0324(11) 0.0393(12) 0.0259(11) -0.0069(9) 0.0017(9) 0.0007(9) O1' 0.0358(11) 0.0262(10) 0.0327(12) -0.0027(9) -0.0023(9) 0.0082(9) O2' 0.106(2) 0.0649(18) 0.0314(14) -0.0022(13) -0.0069(15) 0.0459(18) O3' 0.0315(10) 0.0307(10) 0.0240(10) -0.0018(8) 0.0088(9) 0.0037(9) O4' 0.0734(17) 0.0389(13) 0.0311(13) 0.0029(10) 0.0206(12) 0.0055(12) O5' 0.088(2) 0.0283(12) 0.0396(14) -0.0019(10) 0.0294(14) 0.0023(13) C1 0.0261(14) 0.0299(15) 0.0404(17) 0.0017(13) 0.0045(13) 0.0007(12) C2 0.0336(16) 0.0289(15) 0.0371(17) 0.0012(13) 0.0090(13) -0.0004(13) C3 0.0360(16) 0.0288(15) 0.0295(16) -0.0037(12) 0.0097(13) -0.0047(13) C4 0.0306(15) 0.0392(17) 0.0286(16) -0.0050(13) 0.0034(12) -0.0068(13) C5 0.0240(14) 0.0330(15) 0.0240(14) -0.0032(12) 0.0033(11) -0.0017(12) C6 0.0231(14) 0.0434(18) 0.0341(17) 0.0019(14) 0.0005(12) -0.0016(13) C7 0.0228(14) 0.0418(17) 0.0323(16) 0.0037(14) 0.0002(12) 0.0052(12) C8 0.0255(14) 0.0279(14) 0.0238(14) 0.0016(12) 0.0050(11) -0.0016(11) C9 0.0227(13) 0.0322(15) 0.0215(14) -0.0003(12) 0.0061(11) 0.0008(11) C10 0.0215(13) 0.0292(14) 0.0320(16) -0.0023(12) 0.0060(11) -0.0008(11) C11 0.0232(14) 0.0280(15) 0.0368(17) 0.0024(12) 0.0076(12) 0.0028(11) C12 0.0197(13) 0.0332(15) 0.0233(14) -0.0001(12) 0.0067(11) 0.0038(11) C13 0.0255(13) 0.0294(14) 0.0198(14) 0.0006(11) 0.0060(11) 0.0021(11) C14 0.0231(13) 0.0305(14) 0.0231(14) 0.0015(12) 0.0042(11) 0.0066(11) C15 0.0292(15) 0.0337(16) 0.0355(17) 0.0040(13) -0.0003(13) 0.0069(13) C16 0.0395(17) 0.0321(16) 0.0420(19) 0.0028(14) -0.0020(15) 0.0056(13) C17 0.0325(15) 0.0324(15) 0.0202(14) 0.0000(12) 0.0057(12) 0.0039(12) C18 0.0410(16) 0.0367(16) 0.0250(15) 0.0025(13) 0.0066(13) -0.0058(14) C19 0.0352(16) 0.0352(16) 0.0381(18) -0.0057(14) 0.0139(14) -0.0045(14) C20 0.0349(16) 0.0308(16) 0.0276(16) -0.0032(12) 0.0044(13) 0.0013(13) C21 0.0412(17) 0.0337(17) 0.0419(19) -0.0037(14) 0.0082(15) -0.0068(14) C22 0.0373(16) 0.0329(16) 0.0235(15) -0.0006(12) 0.0086(13) -0.0034(13) C23 0.050(2) 0.0362(17) 0.0410(19) -0.0029(15) 0.0190(16) -0.0119(15) C24 0.0400(17) 0.0342(16) 0.0416(19) 0.0012(14) 0.0079(15) -0.0057(14) C25 0.0288(14) 0.0392(17) 0.0272(15) 0.0000(13) 0.0008(12) -0.0069(13) C26 0.0297(15) 0.057(2) 0.043(2) -0.0010(17) 0.0058(14) 0.0043(16) C27 0.075(3) 0.051(2) 0.069(3) 0.000(2) 0.042(2) -0.012(2) C28 0.057(2) 0.046(2) 0.0297(18) -0.0083(15) -0.0017(16) -0.0170(17) C29 0.0293(16) 0.048(2) 0.045(2) 0.0024(16) 0.0031(14) -0.0080(15) C30 0.0292(14) 0.0318(15) 0.0294(16) -0.0049(12) 0.0087(12) 0.0038(12) C31 0.0314(15) 0.0427(18) 0.0307(17) 0.0052(14) 0.0002(13) -0.0083(14) C32 0.0358(17) 0.0411(18) 0.048(2) 0.0078(16) 0.0030(15) -0.0123(15) C33 0.0263(14) 0.0368(16) 0.0289(16) -0.0001(13) -0.0005(12) 0.0065(12) C34 0.0273(14) 0.0493(19) 0.0358(17) 0.0009(15) 0.0040(13) 0.0037(14) C1' 0.0305(14) 0.0261(14) 0.0289(15) 0.0004(12) 0.0067(12) 0.0020(12) C2' 0.0330(16) 0.0271(15) 0.0327(16) 0.0010(12) 0.0052(13) 0.0003(12) C3' 0.0320(15) 0.0248(14) 0.0318(16) -0.0038(12) -0.0037(12) 0.0056(12) C4' 0.0264(14) 0.0339(16) 0.0316(16) -0.0003(13) 0.0032(12) 0.0021(12) C5' 0.0243(14) 0.0303(15) 0.0289(15) 0.0000(12) 0.0018(11) 0.0020(12) C6' 0.0316(15) 0.0384(17) 0.0402(18) 0.0042(14) 0.0089(14) 0.0059(13) C7' 0.0302(16) 0.0339(16) 0.0413(18) 0.0034(14) 0.0072(14) -0.0015(13) C8' 0.0270(14) 0.0254(14) 0.0261(15) 0.0007(12) -0.0011(12) 0.0003(11) C9' 0.0277(14) 0.0244(14) 0.0198(14) -0.0032(11) -0.0033(11) -0.0006(11) C10' 0.0239(13) 0.0244(14) 0.0242(14) -0.0028(11) -0.0011(11) -0.0004(11) C11' 0.0309(14) 0.0234(14) 0.0298(16) 0.0028(12) 0.0022(12) 0.0001(12) C12' 0.0344(15) 0.0276(14) 0.0229(15) -0.0002(12) 0.0043(12) 0.0039(12) C13' 0.0341(15) 0.0245(14) 0.0217(14) -0.0010(11) -0.0031(12) 0.0014(12) C14' 0.0300(15) 0.0251(14) 0.0285(15) 0.0011(12) -0.0035(12) -0.0024(12) C15' 0.0367(16) 0.0287(15) 0.0413(18) 0.0048(14) 0.0008(14) -0.0047(14) C16' 0.0373(17) 0.0276(16) 0.058(2) 0.0037(15) 0.0041(16) -0.0049(13) C17' 0.0474(18) 0.0238(15) 0.0309(17) -0.0004(12) -0.0001(14) 0.0008(13) C18' 0.0435(17) 0.0335(15) 0.0229(15) -0.0009(13) 0.0003(13) 0.0021(14) C19' 0.0322(15) 0.0324(15) 0.0356(17) -0.0108(13) -0.0040(13) 0.0023(13) C20' 0.0500(19) 0.0253(15) 0.0319(17) -0.0019(13) 0.0125(15) 0.0023(14) C21' 0.062(2) 0.0280(17) 0.056(2) -0.0025(15) 0.0136(19) 0.0053(16) C22' 0.0382(17) 0.0358(17) 0.0407(18) 0.0041(14) 0.0155(14) 0.0086(14) C23' 0.0409(19) 0.044(2) 0.066(2) 0.0035(18) 0.0126(18) 0.0141(16) C24' 0.0390(18) 0.060(2) 0.061(3) 0.000(2) 0.0108(18) 0.0168(18) C25' 0.060(2) 0.115(3) 0.066(2) 0.009(2) 0.0154(18) 0.057(2) C26' 0.070(3) 0.138(4) 0.077(3) -0.003(3) -0.004(2) 0.056(3) C27' 0.078(3) 0.113(3) 0.074(3) 0.030(3) 0.030(2) 0.057(3) C28' 0.0373(17) 0.0372(17) 0.0320(17) -0.0019(14) 0.0053(13) 0.0129(14) C29' 0.0286(16) 0.0385(18) 0.058(2) 0.0022(16) 0.0025(15) 0.0065(13) C30' 0.0423(18) 0.0265(15) 0.0413(19) -0.0019(14) -0.0099(15) -0.0022(13) C31' 0.0431(17) 0.0327(16) 0.0334(18) 0.0002(14) -0.0036(14) 0.0070(14) C32' 0.0365(16) 0.0289(16) 0.047(2) 0.0006(14) -0.0052(15) 0.0027(13) C33' 0.051(2) 0.0257(15) 0.039(2) -0.0010(14) 0.0197(16) 0.0056(14) C34' 0.044(2) 0.056(2) 0.069(3) 0.012(2) 0.0331(19) 0.0145(18) C1S 0.047(3) 0.107(6) 0.062(4) 0.027(5) 0.002(3) -0.010(4) Cl1 0.0417(19) 0.0650(14) 0.0734(19) -0.0028(13) 0.0221(16) -0.0046(12) Cl2 0.0323(6) 0.1050(15) 0.0532(9) -0.0138(9) -0.0067(6) 0.0133(7) C1'S 0.036(5) 0.033(5) 0.049(6) 0.012(5) -0.003(5) -0.004(5) Cl1' 0.036(4) 0.133(8) 0.089(6) 0.006(5) -0.025(3) -0.010(4) Cl2' 0.125(5) 0.157(7) 0.203(8) 0.123(6) 0.087(5) 0.075(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C31 1.340(4) . ? O1 C3 1.459(4) . ? O2 C31 1.205(4) . ? O3 C33 1.330(4) . ? O3 C12 1.470(3) . ? O4 C33 1.199(4) . ? O5 C20 1.438(4) . ? O5 H5 0.8400 . ? O1' C31' 1.337(4) . ? O1' C3' 1.466(3) . ? O2' C31' 1.199(4) . ? O3' C33' 1.330(4) . ? O3' C12' 1.458(4) . ? O4' C33' 1.215(4) . ? O5' C20' 1.438(4) . ? O5' H5' 0.8400 . ? C1 C2 1.524(4) . ? C1 C10 1.544(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.525(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.535(5) . ? C3 H3 1.0000 . ? C4 C28 1.533(4) . ? C4 C29 1.542(4) . ? C4 C5 1.555(4) . ? C5 C6 1.532(4) . ? C5 C10 1.564(4) . ? C5 H5A 1.0000 . ? C6 C7 1.525(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.539(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.552(4) . ? C8 C18 1.560(4) . ? C8 C14 1.567(4) . ? C9 C11 1.528(4) . ? C9 C10 1.566(4) . ? C9 H9 1.0000 . ? C10 C19 1.549(4) . ? C11 C12 1.527(4) . ? C11 H11C 0.9900 . ? C11 H11D 0.9900 . ? C12 C13 1.512(4) . ? C12 H12 1.0000 . ? C13 C17 1.543(4) . ? C13 C14 1.561(4) . ? C13 H13 1.0000 . ? C14 C15 1.539(4) . ? C14 C30 1.559(4) . ? C15 C16 1.541(5) . ? C15 H15C 0.9900 . ? C15 H15D 0.9900 . ? C16 C17 1.543(4) . ? C16 H16C 0.9900 . ? C16 H16D 0.9900 . ? C17 C20 1.551(4) . ? C17 H17 1.0000 . ? C18 H18D 0.9800 . ? C18 H18E 0.9800 . ? C18 H18F 0.9800 . ? C19 H19D 0.9800 . ? C19 H19E 0.9800 . ? C19 H19F 0.9800 . ? C20 C22 1.531(4) . ? C20 C21 1.542(4) . ? C21 H21D 0.9800 . ? C21 H21E 0.9800 . ? C21 H21F 0.9800 . ? C22 C23 1.525(4) . ? C22 H22C 0.9900 . ? C22 H22D 0.9900 . ? C23 C24 1.502(5) . ? C23 H23C 0.9900 . ? C23 H23D 0.9900 . ? C24 C25 1.327(5) . ? C24 H24 0.9500 . ? C25 C26 1.498(5) . ? C25 C27 1.502(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28D 0.9800 . ? C28 H28E 0.9800 . ? C28 H28F 0.9800 . ? C29 H29D 0.9800 . ? C29 H29E 0.9800 . ? C29 H29F 0.9800 . ? C30 H30D 0.9800 . ? C30 H30E 0.9800 . ? C30 H30F 0.9800 . ? C31 C32 1.505(5) . ? C32 H32D 0.9800 . ? C32 H32E 0.9800 . ? C32 H32F 0.9800 . ? C33 C34 1.509(4) . ? C34 H34D 0.9800 . ? C34 H34E 0.9800 . ? C34 H34F 0.9800 . ? C1' C2' 1.531(4) . ? C1' C10' 1.539(4) . ? C1' H1'1 0.9900 . ? C1' H1'2 0.9900 . ? C2' C3' 1.511(4) . ? C2' H2'1 0.9900 . ? C2' H2'2 0.9900 . ? C3' C4' 1.529(4) . ? C3' H3' 1.0000 . ? C4' C28' 1.536(5) . ? C4' C29' 1.542(4) . ? C4' C5' 1.559(4) . ? C5' C6' 1.529(4) . ? C5' C10' 1.559(4) . ? C5' H5'1 1.0000 . ? C6' C7' 1.532(5) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C7' C8' 1.540(4) . ? C7' H7'1 0.9900 . ? C7' H7'2 0.9900 . ? C8' C18' 1.544(4) . ? C8' C9' 1.563(4) . ? C8' C14' 1.570(4) . ? C9' C11' 1.528(4) . ? C9' C10' 1.566(4) . ? C9' H9' 1.0000 . ? C10' C19' 1.541(4) . ? C11' C12' 1.546(4) . ? C11' H11A 0.9900 . ? C11' H11B 0.9900 . ? C12' C13' 1.516(4) . ? C12' H12' 1.0000 . ? C13' C17' 1.542(4) . ? C13' C14' 1.556(4) . ? C13' H13' 1.0000 . ? C14' C15' 1.547(4) . ? C14' C30' 1.551(4) . ? C15' C16' 1.547(5) . ? C15' H15A 0.9900 . ? C15' H15B 0.9900 . ? C16' C17' 1.555(5) . ? C16' H16A 0.9900 . ? C16' H16B 0.9900 . ? C17' C20' 1.545(5) . ? C17' H17' 1.0000 . ? C18' H18A 0.9800 . ? C18' H18B 0.9800 . ? C18' H18C 0.9800 . ? C19' H19A 0.9800 . ? C19' H19B 0.9800 . ? C19' H19C 0.9800 . ? C20' C22' 1.513(5) . ? C20' C21' 1.540(5) . ? C21' H21A 0.9800 . ? C21' H21B 0.9800 . ? C21' H21C 0.9800 . ? C22' C23' 1.531(5) . ? C22' H22A 0.9900 . ? C22' H22B 0.9900 . ? C23' C24' 1.485(6) . ? C23' H23A 0.9900 . ? C23' H23B 0.9900 . ? C24' C25' 1.334(7) . ? C24' H24' 0.9500 . ? C25' C26' 1.483(9) . ? C25' C27' 1.538(9) . ? C26' H26D 0.9800 . ? C26' H26E 0.9800 . ? C26' H26F 0.9800 . ? C27' H27D 0.9800 . ? C27' H27E 0.9800 . ? C27' H27F 0.9800 . ? C28' H28A 0.9800 . ? C28' H28B 0.9800 . ? C28' H28C 0.9800 . ? C29' H29A 0.9800 . ? C29' H29B 0.9800 . ? C29' H29C 0.9800 . ? C30' H30A 0.9800 . ? C30' H30B 0.9800 . ? C30' H30C 0.9800 . ? C31' C32' 1.493(4) . ? C32' H32A 0.9800 . ? C32' H32B 0.9800 . ? C32' H32C 0.9800 . ? C33' C34' 1.500(6) . ? C34' H34A 0.9800 . ? C34' H34B 0.9800 . ? C34' H34C 0.9800 . ? C1S Cl2 1.717(7) . ? C1S Cl1 1.766(7) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C1'S Cl2' 1.723(13) . ? C1'S Cl1' 1.805(14) . ? C1'S H1'A 0.9900 . ? C1'S H1'B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 O1 C3 119.3(2) . . ? C33 O3 C12 119.3(2) . . ? C20 O5 H5 109.5 . . ? C31' O1' C3' 117.0(2) . . ? C33' O3' C12' 118.8(3) . . ? C20' O5' H5' 109.5 . . ? C2 C1 C10 113.7(3) . . ? C2 C1 H1A 108.8 . . ? C10 C1 H1A 108.8 . . ? C2 C1 H1B 108.8 . . ? C10 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C1 C2 C3 110.6(2) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? O1 C3 C2 106.4(2) . . ? O1 C3 C4 109.0(3) . . ? C2 C3 C4 114.2(2) . . ? O1 C3 H3 109.0 . . ? C2 C3 H3 109.0 . . ? C4 C3 H3 109.0 . . ? C28 C4 C3 111.6(3) . . ? C28 C4 C29 107.4(3) . . ? C3 C4 C29 106.7(3) . . ? C28 C4 C5 115.5(3) . . ? C3 C4 C5 106.4(2) . . ? C29 C4 C5 108.9(3) . . ? C6 C5 C4 114.0(2) . . ? C6 C5 C10 110.8(2) . . ? C4 C5 C10 116.6(2) . . ? C6 C5 H5A 104.7 . . ? C4 C5 H5A 104.7 . . ? C10 C5 H5A 104.7 . . ? C7 C6 C5 111.1(3) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 113.2(2) . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 109.3(2) . . ? C7 C8 C18 107.1(2) . . ? C9 C8 C18 112.3(2) . . ? C7 C8 C14 111.5(2) . . ? C9 C8 C14 107.0(2) . . ? C18 C8 C14 109.8(2) . . ? C11 C9 C8 111.2(2) . . ? C11 C9 C10 112.8(2) . . ? C8 C9 C10 116.5(2) . . ? C11 C9 H9 105.0 . . ? C8 C9 H9 105.0 . . ? C10 C9 H9 105.0 . . ? C1 C10 C19 107.8(2) . . ? C1 C10 C5 107.2(2) . . ? C19 C10 C5 114.0(3) . . ? C1 C10 C9 108.4(2) . . ? C19 C10 C9 112.9(2) . . ? C5 C10 C9 106.3(2) . . ? C12 C11 C9 116.1(2) . . ? C12 C11 H11C 108.3 . . ? C9 C11 H11C 108.3 . . ? C12 C11 H11D 108.3 . . ? C9 C11 H11D 108.3 . . ? H11C C11 H11D 107.4 . . ? O3 C12 C13 107.6(2) . . ? O3 C12 C11 105.2(2) . . ? C13 C12 C11 113.2(2) . . ? O3 C12 H12 110.2 . . ? C13 C12 H12 110.2 . . ? C11 C12 H12 110.2 . . ? C12 C13 C17 121.4(2) . . ? C12 C13 C14 110.2(2) . . ? C17 C13 C14 103.6(2) . . ? C12 C13 H13 107.0 . . ? C17 C13 H13 107.0 . . ? C14 C13 H13 107.0 . . ? C15 C14 C30 106.5(2) . . ? C15 C14 C13 101.3(2) . . ? C30 C14 C13 109.8(2) . . ? C15 C14 C8 116.3(2) . . ? C30 C14 C8 112.5(2) . . ? C13 C14 C8 109.7(2) . . ? C14 C15 C16 106.0(2) . . ? C14 C15 H15C 110.5 . . ? C16 C15 H15C 110.5 . . ? C14 C15 H15D 110.5 . . ? C16 C15 H15D 110.5 . . ? H15C C15 H15D 108.7 . . ? C15 C16 C17 107.8(3) . . ? C15 C16 H16C 110.1 . . ? C17 C16 H16C 110.1 . . ? C15 C16 H16D 110.1 . . ? C17 C16 H16D 110.1 . . ? H16C C16 H16D 108.5 . . ? C13 C17 C16 101.5(2) . . ? C13 C17 C20 118.6(2) . . ? C16 C17 C20 115.2(3) . . ? C13 C17 H17 106.9 . . ? C16 C17 H17 106.9 . . ? C20 C17 H17 106.9 . . ? C8 C18 H18D 109.5 . . ? C8 C18 H18E 109.5 . . ? H18D C18 H18E 109.5 . . ? C8 C18 H18F 109.5 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? C10 C19 H19D 109.5 . . ? C10 C19 H19E 109.5 . . ? H19D C19 H19E 109.5 . . ? C10 C19 H19F 109.5 . . ? H19D C19 H19F 109.5 . . ? H19E C19 H19F 109.5 . . ? O5 C20 C22 105.5(2) . . ? O5 C20 C21 108.2(3) . . ? C22 C20 C21 111.1(3) . . ? O5 C20 C17 109.2(2) . . ? C22 C20 C17 113.1(2) . . ? C21 C20 C17 109.6(3) . . ? C20 C21 H21D 109.5 . . ? C20 C21 H21E 109.5 . . ? H21D C21 H21E 109.5 . . ? C20 C21 H21F 109.5 . . ? H21D C21 H21F 109.5 . . ? H21E C21 H21F 109.5 . . ? C23 C22 C20 114.8(3) . . ? C23 C22 H22C 108.6 . . ? C20 C22 H22C 108.6 . . ? C23 C22 H22D 108.6 . . ? C20 C22 H22D 108.6 . . ? H22C C22 H22D 107.5 . . ? C24 C23 C22 113.0(3) . . ? C24 C23 H23C 109.0 . . ? C22 C23 H23C 109.0 . . ? C24 C23 H23D 109.0 . . ? C22 C23 H23D 109.0 . . ? H23C C23 H23D 107.8 . . ? C25 C24 C23 129.5(3) . . ? C25 C24 H24 115.3 . . ? C23 C24 H24 115.3 . . ? C24 C25 C26 122.0(3) . . ? C24 C25 C27 123.6(3) . . ? C26 C25 C27 114.3(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C4 C28 H28D 109.5 . . ? C4 C28 H28E 109.5 . . ? H28D C28 H28E 109.5 . . ? C4 C28 H28F 109.5 . . ? H28D C28 H28F 109.5 . . ? H28E C28 H28F 109.5 . . ? C4 C29 H29D 109.5 . . ? C4 C29 H29E 109.5 . . ? H29D C29 H29E 109.5 . . ? C4 C29 H29F 109.5 . . ? H29D C29 H29F 109.5 . . ? H29E C29 H29F 109.5 . . ? C14 C30 H30D 109.5 . . ? C14 C30 H30E 109.5 . . ? H30D C30 H30E 109.5 . . ? C14 C30 H30F 109.5 . . ? H30D C30 H30F 109.5 . . ? H30E C30 H30F 109.5 . . ? O2 C31 O1 124.7(3) . . ? O2 C31 C32 124.8(3) . . ? O1 C31 C32 110.5(3) . . ? C31 C32 H32D 109.5 . . ? C31 C32 H32E 109.5 . . ? H32D C32 H32E 109.5 . . ? C31 C32 H32F 109.5 . . ? H32D C32 H32F 109.5 . . ? H32E C32 H32F 109.5 . . ? O4 C33 O3 124.7(3) . . ? O4 C33 C34 124.6(3) . . ? O3 C33 C34 110.8(2) . . ? C33 C34 H34D 109.5 . . ? C33 C34 H34E 109.5 . . ? H34D C34 H34E 109.5 . . ? C33 C34 H34F 109.5 . . ? H34D C34 H34F 109.5 . . ? H34E C34 H34F 109.5 . . ? C2' C1' C10' 112.8(2) . . ? C2' C1' H1'1 109.0 . . ? C10' C1' H1'1 109.0 . . ? C2' C1' H1'2 109.0 . . ? C10' C1' H1'2 109.0 . . ? H1'1 C1' H1'2 107.8 . . ? C3' C2' C1' 110.5(2) . . ? C3' C2' H2'1 109.5 . . ? C1' C2' H2'1 109.5 . . ? C3' C2' H2'2 109.5 . . ? C1' C2' H2'2 109.5 . . ? H2'1 C2' H2'2 108.1 . . ? O1' C3' C2' 108.7(2) . . ? O1' C3' C4' 107.2(2) . . ? C2' C3' C4' 113.9(2) . . ? O1' C3' H3' 109.0 . . ? C2' C3' H3' 109.0 . . ? C4' C3' H3' 109.0 . . ? C3' C4' C28' 111.9(3) . . ? C3' C4' C29' 107.3(3) . . ? C28' C4' C29' 107.6(3) . . ? C3' C4' C5' 105.9(2) . . ? C28' C4' C5' 114.9(3) . . ? C29' C4' C5' 108.9(3) . . ? C6' C5' C10' 111.0(2) . . ? C6' C5' C4' 114.0(2) . . ? C10' C5' C4' 117.0(2) . . ? C6' C5' H5'1 104.4 . . ? C10' C5' H5'1 104.4 . . ? C4' C5' H5'1 104.4 . . ? C5' C6' C7' 110.4(3) . . ? C5' C6' H6'1 109.6 . . ? C7' C6' H6'1 109.6 . . ? C5' C6' H6'2 109.6 . . ? C7' C6' H6'2 109.6 . . ? H6'1 C6' H6'2 108.1 . . ? C6' C7' C8' 113.1(3) . . ? C6' C7' H7'1 109.0 . . ? C8' C7' H7'1 109.0 . . ? C6' C7' H7'2 109.0 . . ? C8' C7' H7'2 109.0 . . ? H7'1 C7' H7'2 107.8 . . ? C7' C8' C18' 106.6(2) . . ? C7' C8' C9' 110.2(2) . . ? C18' C8' C9' 112.2(2) . . ? C7' C8' C14' 111.5(2) . . ? C18' C8' C14' 111.0(2) . . ? C9' C8' C14' 105.5(2) . . ? C11' C9' C8' 110.4(2) . . ? C11' C9' C10' 113.0(2) . . ? C8' C9' C10' 116.9(2) . . ? C11' C9' H9' 105.1 . . ? C8' C9' H9' 105.1 . . ? C10' C9' H9' 105.1 . . ? C1' C10' C19' 108.5(2) . . ? C1' C10' C5' 107.6(2) . . ? C19' C10' C5' 114.0(2) . . ? C1' C10' C9' 107.4(2) . . ? C19' C10' C9' 112.8(2) . . ? C5' C10' C9' 106.3(2) . . ? C9' C11' C12' 115.8(2) . . ? C9' C11' H11A 108.3 . . ? C12' C11' H11A 108.3 . . ? C9' C11' H11B 108.3 . . ? C12' C11' H11B 108.3 . . ? H11A C11' H11B 107.4 . . ? O3' C12' C13' 107.1(2) . . ? O3' C12' C11' 105.1(2) . . ? C13' C12' C11' 113.8(2) . . ? O3' C12' H12' 110.2 . . ? C13' C12' H12' 110.2 . . ? C11' C12' H12' 110.2 . . ? C12' C13' C17' 118.8(2) . . ? C12' C13' C14' 110.8(2) . . ? C17' C13' C14' 102.8(2) . . ? C12' C13' H13' 108.0 . . ? C17' C13' H13' 108.0 . . ? C14' C13' H13' 108.0 . . ? C15' C14' C30' 106.8(2) . . ? C15' C14' C13' 100.9(2) . . ? C30' C14' C13' 110.9(3) . . ? C15' C14' C8' 116.3(2) . . ? C30' C14' C8' 111.7(2) . . ? C13' C14' C8' 109.6(2) . . ? C14' C15' C16' 104.1(3) . . ? C14' C15' H15A 110.9 . . ? C16' C15' H15A 110.9 . . ? C14' C15' H15B 110.9 . . ? C16' C15' H15B 110.9 . . ? H15A C15' H15B 109.0 . . ? C15' C16' C17' 108.1(3) . . ? C15' C16' H16A 110.1 . . ? C17' C16' H16A 110.1 . . ? C15' C16' H16B 110.1 . . ? C17' C16' H16B 110.1 . . ? H16A C16' H16B 108.4 . . ? C13' C17' C20' 119.4(3) . . ? C13' C17' C16' 101.2(2) . . ? C20' C17' C16' 114.8(3) . . ? C13' C17' H17' 106.9 . . ? C20' C17' H17' 106.9 . . ? C16' C17' H17' 106.9 . . ? C8' C18' H18A 109.5 . . ? C8' C18' H18B 109.5 . . ? H18A C18' H18B 109.5 . . ? C8' C18' H18C 109.5 . . ? H18A C18' H18C 109.5 . . ? H18B C18' H18C 109.5 . . ? C10' C19' H19A 109.5 . . ? C10' C19' H19B 109.5 . . ? H19A C19' H19B 109.5 . . ? C10' C19' H19C 109.5 . . ? H19A C19' H19C 109.5 . . ? H19B C19' H19C 109.5 . . ? O5' C20' C22' 107.7(3) . . ? O5' C20' C21' 108.5(3) . . ? C22' C20' C21' 113.0(3) . . ? O5' C20' C17' 105.4(3) . . ? C22' C20' C17' 113.8(3) . . ? C21' C20' C17' 108.1(3) . . ? C20' C21' H21A 109.5 . . ? C20' C21' H21B 109.5 . . ? H21A C21' H21B 109.5 . . ? C20' C21' H21C 109.5 . . ? H21A C21' H21C 109.5 . . ? H21B C21' H21C 109.5 . . ? C20' C22' C23' 114.3(3) . . ? C20' C22' H22A 108.7 . . ? C23' C22' H22A 108.7 . . ? C20' C22' H22B 108.7 . . ? C23' C22' H22B 108.7 . . ? H22A C22' H22B 107.6 . . ? C24' C23' C22' 113.6(3) . . ? C24' C23' H23A 108.8 . . ? C22' C23' H23A 108.8 . . ? C24' C23' H23B 108.8 . . ? C22' C23' H23B 108.8 . . ? H23A C23' H23B 107.7 . . ? C25' C24' C23' 129.2(5) . . ? C25' C24' H24' 115.4 . . ? C23' C24' H24' 115.4 . . ? C24' C25' C26' 122.5(6) . . ? C24' C25' C27' 122.9(6) . . ? C26' C25' C27' 114.5(5) . . ? C25' C26' H26D 109.5 . . ? C25' C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? C25' C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 109.5 . . ? C25' C27' H27D 109.5 . . ? C25' C27' H27E 109.5 . . ? H27D C27' H27E 109.5 . . ? C25' C27' H27F 109.5 . . ? H27D C27' H27F 109.5 . . ? H27E C27' H27F 109.5 . . ? C4' C28' H28A 109.5 . . ? C4' C28' H28B 109.5 . . ? H28A C28' H28B 109.5 . . ? C4' C28' H28C 109.5 . . ? H28A C28' H28C 109.5 . . ? H28B C28' H28C 109.5 . . ? C4' C29' H29A 109.5 . . ? C4' C29' H29B 109.5 . . ? H29A C29' H29B 109.5 . . ? C4' C29' H29C 109.5 . . ? H29A C29' H29C 109.5 . . ? H29B C29' H29C 109.5 . . ? C14' C30' H30A 109.5 . . ? C14' C30' H30B 109.5 . . ? H30A C30' H30B 109.5 . . ? C14' C30' H30C 109.5 . . ? H30A C30' H30C 109.5 . . ? H30B C30' H30C 109.5 . . ? O2' C31' O1' 123.9(3) . . ? O2' C31' C32' 124.4(3) . . ? O1' C31' C32' 111.7(3) . . ? C31' C32' H32A 109.5 . . ? C31' C32' H32B 109.5 . . ? H32A C32' H32B 109.5 . . ? C31' C32' H32C 109.5 . . ? H32A C32' H32C 109.5 . . ? H32B C32' H32C 109.5 . . ? O4' C33' O3' 123.4(3) . . ? O4' C33' C34' 124.9(3) . . ? O3' C33' C34' 111.7(3) . . ? C33' C34' H34A 109.5 . . ? C33' C34' H34B 109.5 . . ? H34A C34' H34B 109.5 . . ? C33' C34' H34C 109.5 . . ? H34A C34' H34C 109.5 . . ? H34B C34' H34C 109.5 . . ? Cl2 C1S Cl1 113.8(4) . . ? Cl2 C1S H1SA 108.8 . . ? Cl1 C1S H1SA 108.8 . . ? Cl2 C1S H1SB 108.8 . . ? Cl1 C1S H1SB 108.8 . . ? H1SA C1S H1SB 107.7 . . ? Cl2' C1'S Cl1' 100.0(9) . . ? Cl2' C1'S H1'A 111.8 . . ? Cl1' C1'S H1'A 111.8 . . ? Cl2' C1'S H1'B 111.8 . . ? Cl1' C1'S H1'B 111.8 . . ? H1'A C1'S H1'B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 66.33 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.337 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 876476'